(S)-4-Isopropyl-5,5-dimethyl-1,3-oxazolidinethione as chiral auxiliary for the intramolecular sulfur transfer in α,β-unsaturated N-acylimides, promoted by NbCl5

被引：37

作者：

Ortiz, A ^{[1
]}

Quintero, L

Hernández, H

Maldonaldo, S

Mendoza, G

Bernès, S

机构：

[1] Fac Ciencias Quim, Ctr Invest, Puebla 72570, Mexico

[2] Benemerita Univ Autonoma Puebla, Inst Ciencias, Puebla 72570, Mexico

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 06期

关键词：

ASYMMETRIC-SYNTHESIS; ADDITIONS; ACIDS;

D O I：

10.1016/S0040-4039(02)02837-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,3-oxazolidinethi one 4 has been synthesized from (S)-valine and used in the intramolecular sulfur transfer in its N-enoyl derivatives in the presence of NbCl5 as catalyst, which, moreover, works as an indicator of the course of the reaction. The adducts have subsequently been transformed into the corresponding beta-mercapto esters by action of Sm(OTf)(3) in methanol. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：1129 / 1132

页数：4

相关论文

共 15 条

[1]

Bull SD, 1998, SYNLETT, P519

[2] A glycosylation protocol based on activation of glycosyl 2-pyridyl sulfones with samarium triflate [J].

Chang, GX ;

Lowary, TL .

ORGANIC LETTERS, 2000, 2 (11) :1505-1508

[3] HIGHLY ENANTIOSELECTIVE CATALYTIC DIELS-ALDER ADDITION PROMOTED BY A CHIRAL BIS(OXAZOLINE)-MAGNESIUM COMPLEX [J].

COREY, EJ ;

ISHIHARA, K .

TETRAHEDRON LETTERS, 1992, 33 (45) :6807-6810

[4] 4-SUBSTITUTED-5,5-DIMETHYL OXAZOLIDIN-2-ONES AS EFFECTIVE CHIRAL AUXILIARIES FOR ENOLATE ALKYLATIONS AND MICHAEL ADDITIONS [J].

DAVIES, SG ;

SANGANEE, HJ .

TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :671-674

[5] The 'SuperQuat' (R)-4-phenyl-5,5-dimethyl oxazolidin-2-one as an effective chiral auxiliary for conjugate additions:: Asymmetric synthesis of (-)-aplysillamide B. [J].

Davies, SG ;

Sanganee, HJ ;

Szolcsanyi, P .

TETRAHEDRON, 1999, 55 (11) :3337-3354

[6] REACTIVITY OF BETA-AMINO ALCOHOLS WITH CARBON-DISULFIDE - STUDY ON THE SYNTHESIS OF 2-OXAZOLIDINETHIONES AND 2-THIAZOLIDINETHIONES [J].

DELAUNAY, D ;

TOUPET, L ;

LECORRE, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6604-6607

[7] CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA .

TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144

[8] Rare-earth metal triflates in organic synthesis [J].

Kobayashi, S ;

Sugiura, M ;

Kitagawa, H ;

Lam, WWL .

CHEMICAL REVIEWS, 2002, 102 (06) :2227-2302

[9] A new method for the synthesis of 5- and 6-membered 2-thioxo-1,3-O,N-heterocycles [J].

Li, G ;

Ohtani, T .

HETEROCYCLES, 1997, 45 (12) :2471-2474

[10] UNEXPECTED OUTCOME OF NBCL5-PROMOTED SAKURAI REACTION - MECHANISTIC IMPLICATIONS RELEVANT TO C4H7+ SPECIES [J].

MAETA, H ;

NAGASAWA, T ;

HANDA, Y ;

TAKEI, T ;

OSAMURA, Y ;

SUZUKI, K .

TETRAHEDRON LETTERS, 1995, 36 (06) :899-902