N-carbamate-assisted stereoselective synthesis of chiral vicinal amino sulfides

被引：20

作者：

De Paolis, M ^{[1
]}

Blankenstein, J ^{[1
]}

Bois-Choussy, M ^{[1
]}

Zhu, JP ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 07期

关键词：

D O I：

10.1021/ol025743z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Simply mixing amino alcohol A and thiol in toluene and TFA provided the corresponding amino sulfide B in excellent chemical yield and diastereoselectivity. A double S(N)2 process initiated by O-5 participation of the neighboring N-carbamate group was advanced to explain the overall retention of configuration at the chiral benzylic center.

引用

页码：1235 / 1238

页数：4

共 40 条

[1] A SHORT AND SIMPLE SYNTHESIS OF THE THIOGLUCOSE ANALOG OF THE ANTITUMOR AGENT ETOPOSIDE [J].

ALLEVI, P ;

ANASTASIA, M ;

CIUFFREDA, P .

TETRAHEDRON LETTERS, 1991, 32 (47) :6927-6930

[2] 3-Acetoxyaminoquinazolinones (QNHOAc) as aziridinating agents: ring-opening of N-(Q)-substituted aziridines [J].

Atkinson, RS .

TETRAHEDRON, 1999, 55 (06) :1519-1558

[3]

Brownlee R. T. C., 1973, PROGR PHYS ORG CHEM, V10, P1, DOI DOI 10.1002/9780470171899.CH1

[4] NEIGHBOURING GROUP PARTICIPATION [J].

CAPON, B .

QUARTERLY REVIEWS, 1964, 18 (01) :45-111

[5] SYNTHESIS OF 1-(2-HYDROXYARYL)-1,2,3-PROPANETRIOL AND 1-(2-HYDROXYARYL)-2-AMINO-1,3-PROPANEDIOL DERIVATIVES OF EITHER THREO OR ERYTHRO CONFIGURATION [J].

CASIRAGHI, G ;

CORNIA, M ;

RASSU, G .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :4919-4922

[6] Expanding synthetic utilities of asymmetric dihydroxylation reaction:: Conversion of syn-diols to syn-amino alcohols [J].

Cho, GY ;

Ko, SY .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23) :8745-8747

[7]

Christoffers J, 1997, LIEBIGS ANN-RECL, P1353

[8] Enantioselective total synthesis of ecteinascidin 743 [J].

Corey, EJ ;

Gin, DY ;

Kania, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (38) :9202-9203

[9] Cyclic dipeptides.: 3.: Synthesis of methyl (R)-6-[(tert-butoxycarbonyl)amino]-4,5,6,7-tetrahydro-2-methyl-5-oxo-1,4-thiazepine-3-carboxylate and its hexahydro analogues:: Elaboration of a novel dual ACE NEP inhibitor [J].

Crescenza, A ;

Botta, M ;

Corelli, F ;

Santini, A ;

Tafi, A .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3019-3025

[10] Synthesis and cytotoxic and antitumor activity of esters in the 1,2-dihydroxy-1,2-dihydroacronycine series [J].

Elomri, A ;

Mitaku, S ;

Michel, S ;

Skaltsounis, AL ;

Tillequin, F ;

Koch, M ;

Pierre, A ;

Guilbaud, N ;

Leonce, S ;

KrausBerthier, L ;

Rolland, Y ;

Atassi, G .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (24) :4762-4766

← 1 2 3 4 →