Highly enantioselective phenylacetylene additions to ketones catalyzed by (S)-BINOL-Ti complex

被引：88

作者：

Zhou, YF ^{[1
]}

Wang, R

Xu, ZQ

Yan, WJ

Liu, L

Kang, YF

Han, ZJ

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, Peoples R China

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 23期

关键词：

D O I：

10.1021/ol0485621

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The readily available and inexpensive (S)-BINOL ligand in combination with Ti((OPr)-Pr-i)(4) is an effective chiral catalyst for the catalytic asymmetric addition of alkynylzinc to unactivated simple ketones. Good to excellent enantioselectivities were achieved. No previous case has been reported successfully using BINOL to catalyze the addition of phenylacetylene to unactivated ketones, and thus the utility of BINOL in asymmetric catalysis is expanded.

引用

页码：4147 / 4149

页数：3

共 22 条

[1] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].

Anand, NK ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688

[2] Insight into the mechanism of the asymmetric addition of alkyl groups to aldehydes catalyzed by titanium - BINOLate species [J].

Balsells, J ;

Davis, TJ ;

Carroll, P ;

Walsh, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) :10336-10348

[3] Expanded-spectrum nonnucleoside reverse transcriptase inhibitors inhibit clinically relevant mutant variants of human immunodeficiency virus type 1 [J].

Corbett, JW ;

Ko, SS ;

Rodgers, JD ;

Jeffrey, S ;

Bacheler, LT ;

Klabe, RM ;

Diamond, S ;

Lai, CM ;

Rabel, SR ;

Saye, JA ;

Adams, SP ;

Trainor, GL ;

Anderson, PS ;

Erickson-Viitanen, SK .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1999, 43 (12) :2893-2897

[4] Enantioselective alkynylation of ketones catalyzed by Zn(salen) complexes [J].

Cozzi, PG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (25) :2895-2898

[5] Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes [J].

Frantz, DE ;

Fässler, R ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1806-1807

[6] The discovery of novel reactivity in the development of C-C bond-forming reactions:: In situ generation of zinc acetylides with ZnII/R3N [J].

Frantz, DE ;

Fässler, R ;

Tomooka, CS ;

Carreira, EM .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :373-381

[7] Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes [J].

Gao, G ;

Moore, D ;

Xie, RG ;

Pu, L .

ORGANIC LETTERS, 2002, 4 (23) :4143-4146

[8] Highly enantioselective alkynylation of α-keto ester:: An efficient method for constructing a chiral tertiary carbon center [J].

Jiang, B ;

Chen, ZL ;

Tang, XX .

ORGANIC LETTERS, 2002, 4 (20) :3451-3453

[9] Enantioselective alkynylation of a prochiral ketone catalyzed by C2-symmetric diamino diols [J].

Jiang, B ;

Feng, Y .

TETRAHEDRON LETTERS, 2002, 43 (16) :2975-2977

[10] Highly enantioselective alkynylzinc addition to aromatic aldehydes catalyzed by self-assembled titanium catalysts [J].

Li, XS ;

Lu, G ;

Kwok, WH ;

Chan, ASC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12636-12637

← 1 2 3 →