Low ligand loading, highly enantioselective addition of phenylacetylene to aromatic ketones catalyzed by Schiff-base amino alcohols

被引：76

作者：

Chen, Chao

Hong, Liang

Xu, Zhao-Qing

Liu, Lei

Wang, Rui ^{[1
]}

机构：

[1] Lanzhou Univ, Sch Life Sci, Dept Biochem & Mol Biol, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 11期

关键词：

D O I：

10.1021/ol060526+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Schiff-base amino alcohols 7a, b derived from (L)-phenylglycine through three simple steps are found to be highly effective for the enantioselective addition of phenylacetylene to aromatic ketones. When the loading of 7b was 1 mol %, an ee value of up to 95% was obtained. However, when 7b was lowered to 0.1 mol %, a high ee value of 85% was still achieved. A practical solution to synthesize the optically active tertiary propargylic alcohols was described.

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收藏

页码：2277 / 2280

页数：4

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[41] First enantioselective addition of diethylzinc and dimethylzinc to prostereogenic ketones catalysed by camphorsulfonamide-titanium alkoxide derivatives [J].

Ramón, DJ ;

Yus, M .

TETRAHEDRON, 1998, 54 (21) :5651-5666

[42] Zn(salen)-catalyzed asymmetric alkynylation of ketones [J].

Saito, B ;

Katsuki, T .

SYNLETT, 2004, (09) :1557-1560

[43]

Shimizu K. D., 1997, ANGEW CHEM INT EDIT, V36, P1704

[44] Asymmetric alkynylation of aldehydes catalyzed by an In(III)/BINOL complex [J].

Takita, R ;

Yakura, K ;

Ohshima, T ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) :13760-13761

[45] Highly enantioselective conjugate additions to α,β-unsaturated ketones catalyzed by a (Salen)Al complex [J].

Taylor, MS ;

Zalatan, DN ;

Lerchner, AM ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1313-1317

[46] Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes [J].

Trost, BM ;

Weiss, AH ;

Jacobi von Wangelin, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :8-9

[47] Highly enantioselective addition of phenylacetylene to aldehydes catalyzed by a β-sulfonamide alcohol-titanium complex [J].

Xu, ZQ ;

Wang, R ;

Xu, JK ;

Da, CS ;

Yan, WJ ;

Chen, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) :5747-5749

[48] Highly enantioselective addition of phenylacetylene to aldehydes catalyzed by a camphorsulfonamide ligand [J].

Xu, ZQ ;

Chen, C ;

Xu, JK ;

Miao, MB ;

Yan, WJ ;

Wang, R .

ORGANIC LETTERS, 2004, 6 (08) :1193-1195

[49] Chiral ligands for asymmetric synthesis:: enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by chiral N-α-pyridylmethyl amino alcohols [J].

Yun, HY ;

Wu, YJ ;

Wu, YS ;

Ding, KL ;

Zhou, Y .

TETRAHEDRON LETTERS, 2000, 41 (52) :10263-10266

[50] Highly enantioselective phenylacetylene additions to ketones catalyzed by (S)-BINOL-Ti complex [J].

Zhou, YF ;

Wang, R ;

Xu, ZQ ;

Yan, WJ ;

Liu, L ;

Kang, YF ;

Han, ZJ .

ORGANIC LETTERS, 2004, 6 (23) :4147-4149

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