Abstract

An organocatalytic diastereoselective direct aldol reaction has been described. Enantiopure 4-oxoazetidine-2-carbaldehydes 1 react with ketones 2 in the presence of l-proline (10 mol%) to provide aldols of type 3 in excellent yields and diastereoselectivities. In contrast to this matched case, the use of d-proline as catalyst provides the opposite diastereoisomer 4 in lower diastereoselectivities in a mismatched case. Possible transition states to explain the observed stereochemistry are proposed.

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