Versatile stereocontrol in kinetic resolution of a diphenylphosphinyl-protected α-amino aldehyde by reaction with chiral phosphonates

被引：20

作者：

Kreuder, R

Rein, T

Reiser, O

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

[2] Tech Univ Denmark, Dept Organ Chem, DK-2800 Lyngby, Denmark

[3] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(97)10428-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In kinetic resolutions of the racemic aldehyde 1 by reaction with chiral phosphonates of type 2, all of which contain the same chiral auxiliary in the same enantiomeric form, any of the four diastereomers 3a, 3b, 4a or 4b can be obtained as the main product by an appropriate choice of reaction parameters (geometric selectivities from 66:34 to 98:2, diastereomer ratios between 93:7 and greater than or equal to 99:1). The switch in stereoselectivity observed when KHMDS or NaHMDS is used as base instead of KHMDS/18-crown-6 is rationalized as resulting from a change in influence of the aldehyde alpha-stereocenter from Felkin-Anh-Eisenstein to chelation control. (C) 1997 Elsevier Science Ltd.

引用

页码：9035 / 9038

页数：4

共 23 条

[1] The asymmetric Horner-Emmons reaction using a benzopyrano-isoxazolidine auxiliary [J].

Abiko, A ;

Masamune, S .

TETRAHEDRON LETTERS, 1996, 37 (07) :1077-1080

[2]

Andersson PG, 1996, SYNLETT, P727

[3] Highly selective synthesis of Z-unsaturated esters by using new Horner-Emmons reagents, ethyl (diarylphosphono)acetates [J].

Ando, K .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :1934-1939

[4] PRACTICAL SYNTHESIS OF Z-UNSATURATED ESTERS BY USING A NEW HORNER-EMMONS REAGENT, ETHYL DIPHENYLPHOSPHONOACETATE [J].

ANDO, K .

TETRAHEDRON LETTERS, 1995, 36 (23) :4105-4108

[5]

Dai WM, 1997, TETRAHEDRON-ASYMMETR, V8, P1979

[6] Diastereofacial selection in nucleophilic additions to unsymmetrically substituted trigonal carbons [J].

Gung, BW .

TETRAHEDRON, 1996, 52 (15) :5263-5301

[7]

Helm-chen G., 1995, HOUBEN WEYL METHODS, VE21a, P1

[8] ASYMMETRIC HORNER-WADSWORTH-EMMONS REACTIONS USING MESO DIALDEHYDES AS SUBSTRATES [J].

KANN, N ;

REIN, T .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3802-3804

[9] Highly cis-selective Horner-Wadsworth-Emmons (HWE) reaction of methyl bis(2,4-difluorophenyl)phosphonoacetate [J].

Kokin, K ;

Motoyoshiya, J ;

Hayashi, S ;

Aoyama, H .

SYNTHETIC COMMUNICATIONS, 1997, 27 (14) :2387-2392

[10]

Kumamoto T, 1997, CHEM PHARM BULL, V45, P753

← 1 2 3 →