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Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones using thiourethane ligands

✍ Scribed by Simon M.W. Bennett; Stephen M. Brown; James P. Muxworthy; Simon Woodward

Book ID: 104260623
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 229 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)02686-0

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✦ Synopsis

In the presence of chiral thiourethane ligands [Cu(MeCN)4]BF4 forms active catalysts for the conjugate addition of MeMgBr, ZnEt2 and AIR3 (R = Me, Et) to non-3-en-2-one, hept-3-en-2-one, and 5-methylhex-3-en-2-one. Enantioselectivities of up to 51% are realised for these difficult substrates; for cyclohex-2-enone an e.e. of 42% is attained.

📜 SIMILAR VOLUMES

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The copper catalyzed conjugate addition of n-butyl Grignard to enones in the presence of chiral ferrocenyl phosphine oxazoline ligands has been studied and found to provide useful levels of asymmetric induction. A comparison of the ferrocene derived ligands 3 and 6 with the corresponding phenyl deri