Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 47, Pages 12921-12924Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201407832
Keywords
cycloaddition; enantioselectivity; Lewis acids; photochemistry; ring expansion
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Funding
- Deutsche Forschungsgemeinschaft (DFG) [GRK 1626]
- Fonds der Chemischen Industrie
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By application of substoichiometric amounts (50 mol%) of a chiral Lewis acid, the intramolecular [2+2] photocycloaddition of the title compounds was achieved with high enantioselectivity (up to 94% ee). Upon cleavage of the cyclobutane ring the resulting tricyclic products underwent ring-expansion reactions under acidic conditions and formed anellated seven- or eight-membered-ring systems without racemization. The ring expansion could be combined with a diastereoselective reduction (triethylsilane) or allylation (allyltrimethylsilane) upon BF3 catalysis (48-87% yield).
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