Enantioselective conjugate additions of organolithiums to BHA enoates mediated by a chiral ligand

被引：41

作者：

Asano, Y ^{[1
]}

Iida, A ^{[1
]}

Tomioka, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 60601, Japan

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(97)10366-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conjugate addition reactions of BHA alkenoates with organolithiums in toluene or toluene-hexane at -78 degrees C were mediated by the chiral ligands 1 and 2 to give the corresponding 3-substituted alkanoates in high ees and high yields. The two ligands are complementary each other, 1 is effective for phenyl-and vinyllithiums to give the adducts in 64-93% ee, while 2 is effective for butyl-and ethyllithiums to give the adducts in 91-99% ee. (C) 1997 Elsevier Science Ltd.

引用

页码：8973 / 8976

页数：4

共 36 条

[1] BEAK A, 1996, ACCOUNTS CHEM RES, V29, P552
[2] BEAK P, 1989, ACCOUNTS CHEM RES, V29, P356
[3] STERICALLY DIRECTED CONJUGATE ADDITION-REACTIONS OF UNSATURATED ESTERS
COOKE, MP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) : 1637 - 1638
[4] ENANTIOSELECTIVE, DIASTEREOSELECTIVE, AND REGIOSELECTIVE ZIRCONIUM-CATALYZED CARBOMAGNESATION OF CYCLIC ETHERS WITH HIGHER ALKYLS OF MAGNESIUM - UTILITY IN SYNTHESIS AND MECHANISTIC IMPLICATIONS
DIDIUK, MT
JOHANNES, CW
MORKEN, JP
HOVEYDA, AH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) : 7097 - 7104
[5] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF BETA-SUBSTITUTED CYCLOALKANECARBOXYLATES
FANG, CL
SUEMUNE, H
SAKAI, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) : 4300 - 4303
[6] ASYMMETRIC CONJUGATE ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL ALPHA,BETA-UNSATURATED ESTERS
FANG, CL
OGAWA, T
SUEMUNE, H
SAKAI, K
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (05) : 389 - 398
[7] A SYNTHESIS OF (-)-TETRAHYDROLIPSTATIN IN WHICH THE RELATIVE STEREOCHEMISTRY IS CONTROLLED BY A PHENYLDIMETHYLSILYL GROUP
FLEMING, I
LAWRENCE, NJ
[J]. TETRAHEDRON LETTERS, 1990, 31 (25) : 3645 - 3648
[8] A ternary complex reagent for an asymmetric reaction of lithium ester enolates with imines
Fujieda, H
Kanai, M
Kambara, T
Iida, A
Tomioka, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (08) : 2060 - 2061
[9] ENANTIOSELECTIVE REACTION OF AN IMINE WITH METHYLLITHIUM CATALYZED BY A CHIRAL LIGAND
INOUE, I
SHINDO, M
KOGA, K
KANAI, M
TOMIOKA, K
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (10) : 2527 - 2533
[10] Asymmetric conjugate addition of organocopper reagents
Kanai, M
Nakagawa, Y
Tomioka, K
[J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1996, 54 (06) : 474 - 480

← 1 2 3 4 →