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5 Intramolecular γ-Hydrogen Abstraction (Yang Reaction)

5 Intramolecular γ-Hydrogen Abstraction (Yang Reaction)

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j 5 Formation of a Four Membered Ring



154





(λ=350nm)



NHAc

COTol



3



*

NHAc



H O



isc



Tol



XXI



77a

3

HO

XXII



H



NHAc



H



H



Tol



NH



CH3



Tol



CH3



Tol



NH



H



OH

O



OH

O

XXIIIb



XXIIIa



79%

NHAc



Tol



AcHN



OH

Tol



O

79



(λ=350nm)



NHAc

COTol



(33)



78a



3



*

NHAc



H O



isc



Tol



77b

3

3



H3 C



NHAc

HO



Tol



H



Tol



H



H

Tol



NH



CH3



OH

O

XXIVa



OH

O

XXIVb



Tol



AcHN



H



NH



O

79



NHAc

OH

Tol

78b



(34)



Scheme 5.15 Norrish type II fragmentation and Yang cyclization

of isoleucine derivatives, illustrating the influence of

conformational equilibria.



between the hydroxyl group and the acetamide function. XXIIIb is additionally

stabilized with respect to XXIIIa by steric hindrance of the methyl group in b position

in the latter conformation. In XXIIIb, the two radical centers are close to each other,

which favors cyclization and leads to the final cyclobutanol derivative 78a. Under the

same reaction conditions, the epimeric product 77b yields the intermediates XXIVa,

b. Due to the same steric interactions, the conformer XXIVa is predominant in this

case (reaction 34). The radical centers are now opposed to each other, which favors

fragmentation (Norrish type II reaction). It is not only the competition between

cyclization and fragmentation that is determined by geometric requirements, but



5.5 Intramolecular g Hydrogen Abstraction (Yang Reaction)



also the hydrogen abstraction in the first step. Recently, the structural parameters in

favor of this transformation were identified by a series of transformations carried out

in crystals [84].

When using UV or sunlight irradiation, the glucose derivative 80 possessing

a a diketone function was transformed into the spirocyclic hydroxyketone 81

(Scheme 5.16, reaction 35) [85]. After electronic excitation, hydrogen abstraction at

the carbohydrate moiety takes place, while the corresponding hydrogen abstraction

in the 5 position is facilitated by a pseudoanomeric effect of the ring oxygen and the

BnO substituent in the 6 position. Cyclization of the biradical intermediate XXV is

directed by hydrogen bond between the hydroxy group and the BnO substituent

in the 6 position, and the final product was obtained in quantitative yield. This

O



OH

5 O



OMe



O



O

BnO



O

BnO



OBn



80



OMe



hν (UV or sunlight)



6

OBn



XXV

HO

O

quant.



O



OBn

OBn



OMe



(35)

OBn



BnO

OBn



81



H

O

N



N



Acetone/H2O



O



82



OH



OH







N



O



XXVI



XXVII



O



(36)

HO



O



HO





N

H

82%



83



N

H



O



N



O

84



Ph



O



Bz



O

H







Ph

N



O

XXX



O



XXVIII



O

H



N

H



O



XXIX



O



H



O



Bz



H

O

85 O



(37)

Ph

N Bz



81%



Scheme 5.16 Yang cyclization leading to cyclobutanol derivatives and b lactams.



j155



j 5 Formation of a Four Membered Ring



156



transformation was carried out with a variety of similar carbohydrate derivatives,

such as hexose derivatives carrying the buta 2,3 dione substituent in the anomeric

position. Irradiation at l ¼ 300 nm of the phthalimidyl substituted adamantane

derivative 82. In the presence of acetone yielded the cyclobutanol derivative 83

(reaction 36) [86]. In this transformation, two Yang cyclizations are involved

and, after excitation of the substrate 82 the biradical intermediate XXVI is formed

(this step is sensitized by acetone). Radical combination then leads to the hydro

xyazetidine XXVII. Cleavage of the half aminal structure in this intermediate leads

to the benzoazepine structure XXVIII. In a second photochemical reaction,

hydrogen abstraction occurs via the ketone function, leading to the biradical

intermediate XXIX; a second Yang cyclization then furnishes the final cyclobutanol

derivative 83.

The latter example (reaction 36) already indicates that the Yang cyclization can also

be used to synthesize four membered heterocycles. After light absorption, the a,b

unsaturated carbonyl compound 84 undergoes intramolecular hydrogen abstraction

at the a position of the carbonyl moiety (reaction 37), leading to the 1,4 biradical

intermediate XXX [87]. A radical combination then efficiently yields the spirocyclic b

lactam derivative 85, and only one stereoisomer is formed in this case. In this

transformation, the a,b unsaturated carbonyl function can be considered as being

vinylogous to a simple ketone.



5.6

Metal-Catalyzed Reactions



Many metal catalyzed reactions are accelerated by light irradiation [88]. In the case

of the Vollhardt reaction [89], which is performed with conveniently available Co

catalysts, the irradiation with visible light is included in the standard conditions. In

a triple [2 ỵ 2 ỵ 2] cycloaddition, the nonaalkyne derivative 86 is transformed into

the [7]Phenylene 87 (Scheme 5.17) [90]. Compound 87, containing six benzo

cyclobutene moieties, is a partial structure of the archimedene C120 88. In this way

a variety of similar benzocyclobutene structures such as helical phenylenes [91] can

be built up.

Four membered rings possessing a large variety of substituents have also been

obtained from the photochemical [2 ỵ 2] photocycloaddition of Fischer type carbene

complexes with alkenes [92]. Most frequently, chromium derivatives have been

transformed. When irradiated, the chromium carbene complexes such as 89

(Scheme 5.18, reaction 38) decompose in order to generate the ketene intermediate

XXXI [93]. The formation of a chromium cyclopropanone intermediate (XXXII) has

also been discussed, where the b lactam 91 is formed in a cycloaddition of the

imidazoline 90 onto 89. This lactam was a key intermediate in the synthesis of

lanthanide ligands such as 92 and 93. The corresponding Gd3 ỵ complexes have been

used as magnetic imaging contrast agents. The reaction can be performed on a

stereoselective basis; typically, reaction of the carbene complex 94 with the chiral

enamine derivative 95 yielded the corresponding cyclobutanone 96 in high diaster



5.7 Other Methods



hν,

CpCo(CO)2

2%



86



87



88

Scheme 5.17 Light supported triple [2 ỵ 2 ỵ 2] cycloaddition.

Synthesis of a [7]Phenylene 87 as partial structure of the

archimedene C120 88.



eoselectivity (reaction 39) [94], with no other stereoisomer being detected. Under

these reaction conditions (CO pressure), chromium can be recovered in up to 90%

yield as chromium hexacarbonyl when the reaction solution is triturated with

methanol (in which chromium hexacarbonyl is insoluble). A number of cyclization

reactions have also been performed; upon irradiation of the aldehyde 97 an intra

molecular addition of the carbonyl function to the intermediately generated ketene

takes place, such that the bicyclic lactone 98 was isolated in good yield (reaction

40) [95]. A seven membered ring was formed during this transformation.



5.7

Other Methods



Four membered rings may be generated in a less systematic manner by a variety of

photochemical transformations, many of which are multistep reactions. In the field

of radical chemistry, the photochemical generation of radical intermediates is

frequently applied such that, when the stereoelectronic requirements are fulfilled,

the cyclization steps lead to four membered rings. The oxime derivative 99 undergoes

photochemical sensitized cleavage at the fragile N O bond (Scheme 5.19, reaction



j157



j 5 Formation of a Four Membered Ring



158



(CO)5Cr



TBSO



TBSO







O



+



(CO)4Cr



OTBS CO, 70 psi

80 °C

89



N

90



O



O

.



or (CO)4Cr



O



XXXI



Cbz

N



O



XXXII



CO2H



(38)



O

NH



N



CO2H

O



OTBS

O



Cbz

N



O



N



CO2H

O

O



O

91



HN



N



HN



O



N



O



CO2H



O

O



N



NH



O

O



,



O



O



O



O

O



72%



O



CO2H



O

O



92

O



HN



N

NH



N



O

CO2H

93

O



O



O



OMe

(CO)5Cr



+



N



Ph







Ph



O



MeO



95



O



67%, > 97% de



hν, CO



O



96



O

H

O



59%



(39)

Ph



CH2Cl2, ZnCl2

97



O



N



CO, 90 psi



94



(CO)5Cr



Ph



(40)



O

98



Scheme 5.18 Photochemical transformations of Fischer type chromium carbene complexes.



41) [96], and the resultant acyl oxyl radical XXXIII rapidly loses CO2, leading to the

carbamoyl radical XXXIV. The latter intermediate undergoes cyclization to yield the

bicyclic radical XXXV. Subsequent reaction with oxygen and toluene (used as a

solvent) finally leads to the bicyclic b lactame 100. The two diastereoisomers were

isolated in a ratio of 5 : 1. Upon UV irradiation, the bridged tricyclic ketone 101



5.7 Other Methods



O

Ph



N







Bn

N



O



O



MAP



O



Ph



O



H



O2,

toluene



N

O



Bn



MAP:



N

O



Bn



MeO



70%

(5:1)



O



H



O





88%

XXXVI



102







(43)



S O

O

XXXVII



103

H

N





S O

O

XXXIX



H



N



N



O



H

(42)



S1



O S N



(41)



O

XXXIV



H



100



101



Bn

N



O



HO

H



XXXV



O



- CO2



O

XXXIII



N



99



H



Bn

N



S O

O

XXXVIII

NH



H

O



H



S

O

104 52%



Scheme 5.19 Four membered ring systems are also generated in

less systematic ways by various multistep transformations.



undergoes a Norrish type I cleavage, leading to the biradical intermediate XXXVI

(reaction 42) [97]. A 1,3 shift then takes place such that the cyclobutanone derivative

102 is formed in high yield by radical combination. It should be pointed out here that

this transformation occurs at the singlet state. Triplet excitation of these compounds

leads to an oxa di p methane rearrangement. The tricyclic system of 102 serves as the

core structure of the sesquiterpene family of protoilludanoids. The S N bond of the

bridgehead sultam 103 was transformed into the tricyclic fenestrane like compound

104 (Compound 104 is not a fenestrane but resembles it. Frequently, such tricyclic

compounds are intermediates in the synthesis of fenestranes.) (reaction 43) [98]. For

this, the following mechanism has been discussed: the reaction starts with photo

chemical cleavage of the S N bond, followed by a radical combination to form the



j159



j 5 Formation of a Four Membered Ring



160



biradical intermediate XXXVII that in turn yields the bicyclic sulfone XXXVIII. A 1,5

hydrogen shift (tautomerization) leads to the dienamine derivative XXXIX, while the

final product 104 is generated by a photochemical disrotatory cyclization.



5.8

Concluding Remarks



Photochemical reactions provide a classical access to four membered ring compounds

that generate major interest in organic synthesis, notably as intermediates in multistep

syntheses. The [2 ỵ 2] photocycloaddition of a,b unsaturated carbonyl and carboxyl

compounds with alkenes and [2 þ 2] photocycloaddition of ketones with alkenes (the

Paternò B€

uchi reaction) are discussed in Chapters 6 and 7, respectively. Yet, aside

from these transformations, a variety of further reactions provides a systematic access

to four membered rings that possess a wide structural variation. Four membered ring

compounds may also be created via less systematic photochemical transformations,

many of which can be carried out without additional chemical activation. As a

consequence, such transformations are rendered not only very convenient but also

extremely interesting within the context of “green chemistry.”



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