Abstract
AbstractTwo achiral diazirines 1a and 1b have been encapsulated in the inherently chiral cavity of α‐cyclodextrin (6‐Cy), β‐cyclodextrin (7‐Cy) and permethylated β‐cyclodextrin (TRIMEB) and photolyzed. Because of supramolecular photochirogenesis the generated carbenes afford intramolecular C–H insertion products not as a racemate but one enantiomer is slightly favored. With 1a@(6‐Cy)2 the ee of product 7a is doubled. To the best of our knowledge for the first time for carbene reactions, products are imprinted, though modestly, with handedness derived from Cys. The reaction of 1b is highly dependent on the molecular reactor used for inclusion. Whereas 7‐Cy is very efficient for favoring dimerization through azine formation, the use of TRIMEB permits exclusive formation of intramolecular insertion product 7b. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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