Synthesis of new enantiopure gamma-aminoalcohols: Their use as catalysts in the alkylation of benzaldehyde by diethylzinc

被引：60

作者：

Cicchi, S

Crea, S

Goti, A

Brandi, A

机构：

[1] Dipto. Chim. Organ. Ugo S., Università di Firenze, Ctro. C.N.R Stud. Composti E., I-50121 Firenze

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 02期

关键词：

D O I：

10.1016/S0957-4166(96)00502-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The straightforward synthesis of new enantiopure gamma-aminoalcohols through 1,3-dipolar cycloadditon to a chiral cyclic nitrone derived from L-malic acid is described. Results of the application of these compounds as chiral catalysts in the alkylation of benzaldehyde with diethylzinc are also reported. (C) 1997 Elsevier Science Ltd.

引用

页码：293 / 301

页数：9

共 24 条

[1] CHO BT, 1994, TETRAHEDRON LETT, V35, P4115
[2] NEW SYNTHESIS OF 5-MEMBERED CYCLIC NITRONES FROM TARTARIC ACID
CICCHI, S
HOLD, I
BRANDI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) : 5274 - 5275
[3] A 5-MEMBERED ENANTIOPURE CYCLIC NITRONE FROM MALIC-ACID BY REGIOSELECTIVE OXIDATION OF CYCLIC HYDROXYLAMINE - SYNTHESIS OF (1S,7S,8AR)-OCTAHYDRO-1,7-DIHYDROXYINDOLIZINE
CICCHI, S
GOTI, A
BRANDI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) : 4743 - 4748
[4] 1,3-AMINOALCOHOLS BY REDUCTIVE CLEAVAGE OF ISOXAZOLIDINES WITH MOLYBDENUM HEXACARBONYL
CICCHI, S
GOTI, A
BRANDI, A
GUARNA, A
DESARLO, F
[J]. TETRAHEDRON LETTERS, 1990, 31 (23) : 3351 - 3354
[5] CONFALONE PN, 1988, ORG REACTIONS, V36, P1
[6] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS
COREY, EJ
BAKSHI, RK
SHIBATA, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5551 - 5553
[7] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES
COREY, EJ
BAKSHI, RK
SHIBATA, S
CHEN, CP
SINGH, VK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) : 7925 - 7926
[8] (+)-1(S),5(R),8(S)-8-PHENYL-2-AZABICYCLO[3.3.0]OCTAN-8-OL N,O-METHYLBORONATE (2) AND ITS ENANTIOMER, CHIRAL CHEMZYMES WHICH SERVE AS CATALYSTS FOR THEIR OWN ENANTIOSELECTIVE SYNTHESIS
COREY, EJ
CHEN, CP
REICHARD, GA
[J]. TETRAHEDRON LETTERS, 1989, 30 (41) : 5547 - 5550
[9] STEREOSPECIFIC SYNTHESIS OF RACEMIC DAUNOSAMINE - DIASTEREOFACIAL SELECTIVITY IN A NITRONE CYCLOADDITION
DESHONG, P
LEGINUS, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (06) : 1686 - 1688
[10] 1,3-DIPOLAR CYCLOADDITION .43. ISOXAZOLIDINE FROM NITRONES WITH ALPHA BETA-UNSATURATED CARBOXYLICESTERS OR NITRILES
HUISGEN, R
HAUCK, H
GRASHEY, R
SEIDL, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (07): : 2568 - &

← 1 2 3 →