Catalytic Asymmetric Conjugate Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-2,4,6-Triisopropylphenylsulfonylaldimines with Use of N-Boc-l-Val-Connected Amidophosphane-Copper(I) Catalyst
- 20 November 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (1) , 297-300
- https://doi.org/10.1021/jo0484225
Abstract
Asymmetric conjugate addition of dialkylzinc to α,β-unsaturated N-2,4,6-triisopropylphenylsulfonylaldimines 9 was catalyzed by 5 mol % N-Boc-l-valine-connected amidophosphane 5a-Cu(MeCN)4BF4 in the presence of 4 Å MS in toluene to afford, after hydrolysis of an imine to an aldehyde through a short alumina column and reduction with sodium borohydride, the corresponding β-alkylated alkanols 10 with 67−91% ee in reasonably high yields.Keywords
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