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?-Siloxy-?-haloketones through highly diastereoselective single and double mukaiyama aldol reactions.

ABSTRACT: Double-action haloketones: A super silyl group enabled the first highly diastereoselective Mukaiyama aldol reactions of ?-chloro- and ?-fluoroketones with a wide range of aldehydes, providing anti-?-siloxy-?-haloketones. This process is compatible with one-pot double-aldol methodology and allows for rapid access to new halogen-modified polyketide fragments bearing up to four contiguous stereocenters.

SUBMITTER: Saadi J

PROVIDER: S-EPMC3874236 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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β-Siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions.

Saadi Jakub J Yamamoto Hisashi H

Chemistry (Weinheim an der Bergstrasse, Germany) 20130219 12

Double-action haloketones: A super silyl group enabled the first highly diastereoselective Mukaiyama aldol reactions of α-chloro- and α-fluoroketones with a wide range of aldehydes, providing anti-β-siloxy-α-haloketones. This process is compatible with one-pot double-aldol methodology and allows for rapid access to new halogen-modified polyketide fragments bearing up to four contiguous stereocenters. ...[more]

PMID: 23424059

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