BINOL-catalyzed highly enantioselective terminal alkyne additions to aromatic aldehydes

被引：181

作者：

Moore, D ^{[1
]}

Pu, L ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 11期

关键词：

D O I：

10.1021/ol025825n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The readily available BINOL ligand in combination with Ti((OPr)-Pr-i)(4) was found to catalyze the highly enantioselective reaction (92-98% ee) of terminal alkynes with aromatic aldehydes that contain a variety of substituents and substitution patterns. After the preparation of the zinc acetylide reagent, the catalytic asymmetric addition to aldehydes proceeded at room temperature with excellent stereocontrol. This simple catalyst system is practical for the asymmetric synthesis of chiral propargylic alcohols.

引用

页码：1855 / 1857

页数：3

共 29 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] 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

[4] 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

[5] 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

[6] A highly general catalyst for the enantioselective reaction of aldehydes with diethylzinc [J].

Huang, WS ;

Hu, QS ;

Pu, L .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1364-1365

[7] 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

[8] CATALYTIC ASYMMETRIC ALLYLATION OF ALDEHYDES [J].

KECK, GE ;

TARBET, KH ;

GERACI, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8467-8468

[9]

LI Z, 1999, TETRAHEDRON-ASYMMETR, P1453

[10] Enantioselective alkynylation of aromatic aldehydes catalyzed by new chiral amino alcohol-based ligands [J].

Lu, G ;

Li, XS ;

Zhou, ZY ;

Chan, WL ;

Chan, ASC .

TETRAHEDRON-ASYMMETRY, 2001, 12 (15) :2147-2152

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