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Issue 8, 2013
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Asymmetric synthesis of propargylic alcohols via aldol reaction of aldehydes with ynals promoted by prolinol ether–transition metal–Brønsted acid cooperative catalysis

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Abstract

A catalytic and highly stereoselective entry to propargylic alcohols and products derived thereof is reported based on an unprecedented cross-aldol coupling between unmodified aldehydes and ynals. The method requires an amine–metal salt–Brønsted acid ternary catalyst system and implies synergistic activation of the donor aldehyde via enamine and of the acceptor carbonyl via unique and reversible metal–alkyne complexation. Specifically, by using a combined α,α-dialkylprolinol silyl ether–CuI–PhCO2H catalyst system, remarkably high levels of diastereo- and enantioselectivity (anti/syn up to >20 : 1, ee up to >99%) are achieved.

Graphical abstract: Asymmetric synthesis of propargylic alcohols via aldol reaction of aldehydes with ynals promoted by prolinol ether–transition metal–Brønsted acid cooperative catalysis

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Publication details

The article was received on 17 Apr 2013, accepted on 20 May 2013 and first published on 21 May 2013


Article type: Edge Article
DOI: 10.1039/C3SC51027A
Citation: Chem. Sci., 2013,4, 3198-3204
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    Asymmetric synthesis of propargylic alcohols via aldol reaction of aldehydes with ynals promoted by prolinol ether–transition metal–Brønsted acid cooperative catalysis

    E. Gómez-Bengoa, J. M. García, S. Jiménez, I. Lapuerta, A. Mielgo, J. M. Odriozola, I. Otazo, J. Razkin, I. Urruzuno, S. Vera, M. Oiarbide and C. Palomo, Chem. Sci., 2013, 4, 3198
    DOI: 10.1039/C3SC51027A

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