Enantioselective alkynylation of a prochiral ketone catalyzed by C2-symmetric diamino diols

被引:53
作者
Jiang, B [1 ]
Feng, Y [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
alkynylation; enantioselective; C-2-symmetric diamino diol; ketone;
D O I
10.1016/S0040-4039(02)00444-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-2-Symmetric diamino diols were used as chiral ligands to induce the asymmetric addition of lithium acetylides to carbonyl groups. The enantiomeric excesses (up to 99% ee) depended on the structure of the acetylene. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2975 / 2977
页数:3
相关论文
共 14 条
[1]   Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes [J].
Boyall, D ;
López, F ;
Sasaki, H ;
Frantz, D ;
Carreira, EM .
ORGANIC LETTERS, 2000, 2 (26) :4233-4236
[2]   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
[3]   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
[4]   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
[5]   Catalytic enantioselective synthesis of secondary alcohols using C2-symmetric diamino diol ligands [J].
Jiang, B ;
Feng, Y ;
Hang, JF .
TETRAHEDRON-ASYMMETRY, 2001, 12 (16) :2323-2329
[6]  
LI Z, 1999, SYNTHESIS-STUTTGART, P143
[7]   CATALYTIC ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE ALKYNYL ALCOHOLS BY ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES AND BY ENANTIOSELECTIVE ALKYLATION OF ALKYNYL ALDEHYDES [J].
NIWA, S ;
SOAI, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :937-943
[8]   CATALYTIC ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE ALKYNYL ALCOHOLS [J].
SOAI, K ;
NIWA, S .
CHEMISTRY LETTERS, 1989, (03) :481-484
[9]  
Tan L, 1999, ANGEW CHEM INT EDIT, V38, P711, DOI 10.1002/(SICI)1521-3773(19990301)38:5<711::AID-ANIE711>3.0.CO
[10]  
2-W