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Diastereoselective Baylis-Hillman Reactions: The Design and Synthesis of a Novel Camphor-Based Chiral Auxiliary.
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Abstract
Reaction of chiral acryloylhydrazide 5 derived from novel auxiliary 4 with aldehydes in the presence of DABCO affords practical levels (up to 98% de) of beta-hydroxy-alpha-methylene carbonyl derivatives, and high optical purity of both diastereomers of 6a-d and 7a-d can be obtained by changing the solvent.