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Acyclic stereoselection. 35. Effect of cation on diastereofacial selectivity in aldol reactions of a chiral α-silyloxy ketone.

✍ Scribed by Clayton H Heathcock; Simeon Arseniyadis

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 228 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)95111-6

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✦ Synopsis

By an appropriate choice of cation, three of the four possible aldols from the reactions of the chiral a-silyloxy ketone 1 with aldehydes may be obtained.

The Z lithium enolate provides 6, the Z boron enolate gives 7, and the E magnesium enolate affords 8.

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