Enantioselective synthesis of α-sulfenylated ketones and aldehydes via α-thiolation of metalated SAMP/RAMP hydrazones

被引：32

作者：

Enders, D ^{[1
]}

Schäfer, T ^{[1
]}

Mies, W ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(98)00481-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric cc-sulfenylation of lithiated SAMP/RAMP hydrazones (S)-2 with disulfides afforded alpha-thiolated hydrazones (S,R)-3 in good yields (48-87%) and high diastereomeric excesses (91-96%). Subsequent oxidative cleavage or acidic hydrolysis of the hydrazones furnished alpha-Dthiolated ketones (R)-4a-d with high enantiomeric excesses (87->96%). alpha-Sulfenylated aldehydes (R)-8a-d were prepared by a similar reaction sequence with 45-93% ee. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：10239 / 10252

页数：14

共 27 条

[1] ASYMMETRIC CATALYSIS .58. ENANTIOSELECTIVE S-H AND C-H INSERTIONS WITH OPTICALLY-ACTIVE RH(II) AND CU(II) CATALYSTS [J].

BRUNNER, H ;

WUTZ, K ;

DOYLE, MP .

MONATSHEFTE FUR CHEMIE, 1990, 121 (10) :755-764

[2] THE SYNTHESIS OF OPTICALLY-ACTIVE 2-PHENYLTHIO ALDEHYDES [J].

CHIBALE, K ;

WARREN, S .

TETRAHEDRON LETTERS, 1994, 35 (23) :3991-3994

[3] 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

[4] (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

[5] ASYMMETRIC SYNTHESIS VIA METALATED CHIRAL HYDRAZONES - ENANTIOSELECTIVE ALKYLATION OF CYCLIC-KETONES AND ALDEHYDES [J].

ENDERS, D ;

EICHENAUER, H .

CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (08) :2933-2960

[6] ASYMMETRIC SYNTHESIS OF ALPHA-SUBSTITUTED KETONES BY METALATION AND ALKYLATION OF CHIRAL HYDRAZONES [J].

ENDERS, D ;

EICHENAUER, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (09) :549-551

[7] 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

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

Enders, D ;

Piva, O ;

Burkamp, F .

TETRAHEDRON, 1996, 52 (08) :2893-2908

[9]

Enders D., 1984, ASYMMETRIC SYNTHES B, V3, P275

[10]

ENDERS D, 1995, ENCY REAGENTS ORGANI, P3368

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