Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes

被引:190
作者
Gao, G
Moore, D
Xie, RG
Pu, L
机构
[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA
[2] Sichuan Univ, Dept Chem, Chengdu, Peoples R China
关键词
D O I
10.1021/ol026921r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The readily available and inexpensive BINOL in combination with Ti((OPr)-Pr-i)(4) is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other alpha,beta-unsaturated aldehydes to generate chiral propargyl alcohols with 91-99% ee at room temperature. No previous chiral catalysts have exhibited such a broad scope of enantioselectivity with respect to the type of aldehydes for this reaction.
引用
收藏
页码:4143 / 4146
页数:4
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共 32 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]   ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF ADDITION-REACTION OF ALLYLIC SILANES AND STANNANES TO GLYOXYLATES BY BINAPHTHOL-DERIVED TITANIUM COMPLEX [J].
AOKI, S ;
MIKAMI, K ;
TERADA, M ;
NAKAI, T .
TETRAHEDRON, 1993, 49 (09) :1783-1792
[3]   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
[4]   HIGHLY ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES PROMOTED BY CHIRAL OXAZABOROLIDINES [J].
COREY, EJ ;
CIMPRICH, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3151-3152
[5]   CATALYTIC ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].
COSTA, AL ;
PIAZZA, MG ;
TAGLIAVINI, E ;
TROMBINI, C ;
UMANIRONCHI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7001-7002
[6]   Enantiodivergent total syntheses of (+)- and (-)-scopadulcic acid A [J].
Fox, ME ;
Li, C ;
Marino, JP ;
Overman, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) :5467-5480
[7]   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
[8]   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
[9]   EFFICIENT LIGANDS, CHIRAL 2-[2,2-DIMETHYL-1-(2-PYRIDYL)PROPOXY]-1,1-DIARYLETHANOLS FOR HIGHLY ENANTIOSELECTIVE ADDITION OF ALKYNYLZINC REAGENTS TO VARIOUS ALDEHYDES [J].
ISHIZAKI, M ;
HOSHINO, O .
TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1901-1904
[10]   Highly enantioselective alkynylation of aldehydes catalyzed by a readily available chiral amino alcohol-based ligand [J].
Jiang, B ;
Chen, ZL ;
Xiong, WN .
CHEMICAL COMMUNICATIONS, 2002, (14) :1524-1525