Enantioselective 1,4‐Addition of Aliphatic <i>Grignard</i> Reagents to Enones Catalyzed by Readily Available Copper(I) thiolates derived from TADDOL. Preliminary communication

Helvetica Chimica Acta - Tập 80 Số 8 - Trang 2515-2519 - 1997
Dieter Seebàch1, Georg Jaeschke1,2, A. Pichota1,3, Laurent Audergon1
1Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule, ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich
2Part of the Ph. D. thesis of G.J., Diss, ETH NO. 12300, 1997.
3Part of the projected Ph. D. thesis of A.P., ETH-Zürich.

Tóm tắt

AbstractTwo simple thiols derived from the parent TADDOL, α,α,α′,α′ tetraphenyl‐2,2‐dimethyl‐1,3‐clioxolan‐4,5‐dimethanol, are used to prepare Cu1 complexes C and D to catalyze (0.05 equiv.) 1,4‐additions of Grignard reagents RMgCl to cyclic enones with enantioselectivities which are comparable to or better than previously reported (enantiomer ratios up to 92:8).

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