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Synlett 2006(3): 0435-0439
DOI: 10.1055/s-2006-926239
DOI: 10.1055/s-2006-926239
LETTER
© Georg Thieme Verlag Stuttgart · New York
The Baylis-Hillman Reaction with Chiral α-Amino Aldehydes under Racemization-Free Conditions
Further Information
Received
26 October 2005
Publication Date:
06 February 2006 (online)
Publication History
Publication Date:
06 February 2006 (online)
Abstract
The Baylis-Hillman reaction with chiral α-amino aldehydes has been revisited. The reaction carried out under the influence of ultrasound avoids the aldehyde racemization almost completely, providing useful chiral substrates which can be used as starting materials for the synthesis of natural products. To demonstrate the synthetic applicability of these adducts, the easy preparation of a bicyclic lactam with an indolizidinic skeleton was accomplished.
Key words
aldehydes - amino aldehydes - alkaloids - ring closure - stereoselectivity
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