Asymmetric synthesis of vicinal thioether alcohols by diastereoselective 1,2-addition of carbon nucleophiles to enantiomerically enriched alpha-sulfenylated aldehydes

被引：27

作者：

Enders, D

Piva, O

Burkamp, F

机构：

[1] Institut für Organische Chemie, Rheinisch-Westfälische TH, D-52074 Aachen

来源：

TETRAHEDRON | 1996年 / 52卷 / 08期

关键词：

D O I：

10.1016/0040-4020(95)01040-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active alpha-sulfenylated aldehydes (S)-1, readily available by asymmetric alkylation of alpha-sulfenylated acetaldehyde-SAMP-hydrazones followed by chemoselective oxidative removal of the chiral auxiliary, can be transformed into vicinal thioether alcohols 2, 5 and 6 by diastereoselective 1,2-addition using various carbon nucleophiles. The final compounds are obtained with high enantiomeric- (ee = 80 - 97%) and diastereomeric excesses (de = 88 - > 95%) in good chemical yields (51 - 88%).

引用

收藏

页码：2893 / 2908

页数：16

相关论文

共 44 条

[11] STEREOCHEMICALLY CONTROLLED SYNTHESIS OF SPIROCYCLIC LACTONES AND ETHERS FROM N-METHYL-4-PIPERIDONE AND 3-QUINUCLIDINONE BY PHENYLTHIO MIGRATION [J].

COLDHAM, I ;

COLLINGTON, EW ;

HALLETT, P ;

WARREN, S .

TETRAHEDRON LETTERS, 1988, 29 (41) :5321-5324

[12] ENANTIOSELECTIVE OXIDATION OF BETA-HYDROXYTHIOETHERS .1. SYNTHESIS OF OPTICALLY-ACTIVE ALCOHOLS AND EPOXIDES [J].

CONTE, V ;

DIFURIA, F ;

LICINI, G ;

MODENA, G ;

SBAMPATO, G ;

VALLE, G .

TETRAHEDRON-ASYMMETRY, 1991, 2 (04) :257-276

[13] ADDITIVE PUMMERER REACTIONS OF VINYLIC SULFOXIDES - SYNTHESIS OF 2-(PHENYLSULPHENYL) ALDEHYDES AND PRIMARY ALCOHOLS [J].

CRAIG, D ;

DANIELS, K ;

MACKENZIE, AR .

TETRAHEDRON LETTERS, 1991, 32 (47) :6973-6976

[14] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[15] ENANTIOSELECTIVE SYNTHESIS OF POLYFUNCTIONAL SMALL BUILDING-BLOCKS WITH A QUATERNARY STEREOGENIC CENTER [J].

ENDERS, D ;

ZAMPONI, A ;

SCHAFER, T ;

NUBLING, C ;

EICHENAUER, H ;

DEMIR, AS ;

RAABE, G .

CHEMISCHE BERICHTE, 1994, 127 (09) :1707-1721

[16] (S)-(-)-1-AMINO-2-(SILOXYMETHYL)PYRROLIDINES - NOVEL AND EFFICIENT REAGENTS FOR CHROMATOGRAPHIC RESOLUTION OF ALPHA-SUBSTITUTED ALDEHYDES [J].

ENDERS, D ;

MIES, W .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (18) :1221-1223

[17] ENANTIOSELECTIVE SYNTHESIS OF 2-SULFENYLATED ALDEHYDES - ALKYLATION OF SULFENYLATED ACETALDEHYDE SAMP-HYDRAZONES [J].

ENDERS, D ;

SCHAFER, T ;

PIVA, O ;

ZAMPONI, A .

TETRAHEDRON, 1994, 50 (11) :3349-3362

[18]

ENDERS D, UNPUB

[19] ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES - AN EFFICIENT SYNTHESIS OF (R)-3,4-EPOXY-1-BUTANOL AND (S)-3,4-EPOXY-1-BUTANOL [J].

FERINGA, BL ;

DELANGE, B .

TETRAHEDRON, 1988, 44 (23) :7213-7222

[20] EITHER DIASTEREOFACIAL DIFFERENTIATION IN THE REACTION OF CHIRAL THIOMETHYLKETONES WITH APPROPRIATE ORGANOMETALLICS [J].

FUJISAWA, T ;

TAKEMURA, I ;

UKAJI, Y .

TETRAHEDRON LETTERS, 1990, 31 (38) :5479-5482

← 1 2 3 4 5 →