Photoaddition of olefins to cyclic imides: intermolecular oxetane formation and ring expansion

Kanaoka, Yuichi; Yoshida, Kenji; Hatanaka, Y.

doi:10.1021/jo01318a053

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1997

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Cited by 25 publications

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“…The reaction is regiospecific [equation (38)] (24) and stereospecific [equation (39)]. <43) It also occurs with conjugated dienes, and the reaction between N-methylphthalimide and butadiene [equation (40)] was the first reported example(44) of this unexpected photoaddition process. With the conjugated diene the product isolated in very high yield has undergone a shift of the double bond compared with the structure expected on the basis of the alkene photoproducts.…”

Section: %mentioning

confidence: 99%

Phthalimide and Its Derivatives

Coyle

1984

Synthetic Organic Photochemistry

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Section: %mentioning

confidence: 99%

Phthalimide and Its Derivatives

Coyle

1984

Synthetic Organic Photochemistry

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“…Only partial conversion to 8 was observed when 7 reacted with dichloroisocyanuric acid under alkaline conditions. Reaction of 7 with iodobenzene bis(trifluoroacetate)/pyridine produced 8 in about 40% isolated yield. Finally, we found that the Hofmann degradation of asparagine 7 with iodosobenzene diacetate provided the desired product 8 in 75% yield.…”

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The Enantiospecific Synthesis of an Isoxazoline. A RGD Mimic Platelet GPIIb/IIIa Antagonist

et al. 1997

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A convergent, large-scale, chiral synthesis of isoxazoline 1 has been achieved in 37% overall yield and >99.6% optical purity, starting from L-asparagine and 4-cyanobenzaldehyde. Hofmann reaction of N(alpha)-n-Boc-L-asparagine with iodosobenzene diacetate provides optically pure N(alpha)-n-Boc-L-alpha,beta-diaminopropionic acid (8) in 75% yield. A process of lipase resolution-base catalyzed epimerization gives the single enantiomer 5. Reaction of acid 5 with amine 9 in the presence of thionyl chloride forms the framework of 1. A Pinner reaction of intermediate 4 in methyl acetate or anisole, followed by an amidination with ammonium acetate, gives optically pure product 1.

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