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Tandem Mukaiyama Michael-aldol reactions catalyzed by samarium diiodide

✍ Scribed by Nicolas Giuseppone; Yann Courtaux; Jacqueline Collin

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 217 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01724-9

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✦ Synopsis

Samarium diiodide catalyzes a one pot procedure allowing to perform sequentially the Mukaiyama-Michael addition of a ketene silyl acetal on a cyclic ~,~-unsaturated ketone, followed by a Mukaiyama aldol reaction of an aldehyde. The adducts are isolated as silyl ethers in good yields and in most cases with high diastereoselectivity.

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