Asymmetric synthesis of α-mercapto-β-amino acid derivatives:: application to the synthesis of polysubstituted thiomorpholines

被引：16

作者：

Candela-Lena, Jose I. ^{[1
]}

Davies, Stephen G. ^{[1
]}

Roberts, Paul M. ^{[1
]}

Roux, Bruno ^{[1
]}

Russell, Angela J. ^{[1
]}

Sanchez-Fernandez, Elena M. ^{[1
]}

Smith, Andrew D. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Organ Chem, Oxford OX1 3TA, England

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 07期

关键词：

D O I：

10.1016/j.tetasy.2006.04.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Tandem conjugate addition of homochiral lithium N-benzyl-N-(alpha-methyl-p-methoxybenzyl)amide to tert-butyl cinnamate and enolate trapping with (TsSBu)-Bu-t proceeds with high diastercoselectivity to give a homochiral anti-alpha-tert-butylthio-beta-amino ester. Stepwise deprotection gives the corresponding free alpha-tert-butylthio-beta-amino acid without epimerisation. Tandem conjugate addition of homochiral lithium N-allyl-N-(alpha-methylbenzyl)amide to tert-butyl cinnamate and enolate trapping with TsS'Bu followed by conversion of the S-tert-butyl group to a disulphide, and reduction with Lalancette's reagent generates polysubstituted thiomorpholine derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：1135 / 1145

页数：11

共 42 条

[1] Ruthenium-catalyzed chemoselective N-allyl cleavage: Novel Grubbs carbene mediated deprotection of allylic amines [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (23) :5793-5799

[2] Partial protection against botulinum B neurotoxin-induced blocking of exocytosis by a potent inhibitor of its metallopeptidase activity [J].

Anne, C ;

Turcaud, S ;

Blommaert, AGS ;

Darchen, F ;

Johnson, EA ;

Roques, BR .

CHEMBIOCHEM, 2005, 6 (08) :1375-1380

[3] Thio-derived disulfides as potent inhibitors of botulinum neurotoxin type B: Implications for zinc interaction [J].

Anne, C ;

Blommaert, A ;

Turcaud, S ;

Martin, AS ;

Meudal, H ;

Roques, BP .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (21) :4655-4660

[4] Development of potent inhibitors of botulinum neurotoxin type B [J].

Anne, C ;

Turcaud, S ;

Quancard, J ;

Teffo, F ;

Meudal, H ;

Fournié-Zaluski, MC ;

Roques, BP .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (22) :4648-4656

[5] METAL-AMIDES IN ORGANIC-SYNTHESIS .7. STEREODIVERGENT SYNTHESIS OF THE ENOLATES OF A BETA-AMINO ESTER BY USING LITHIUM N-BENZYLTRIMETHYLSILYLAMIDE [J].

ASAO, N ;

UYEHARA, T ;

YAMAMOTO, Y .

TETRAHEDRON, 1990, 46 (13-14) :4563-4572

[6] Preparation of substituted indolines via anionic cyclization [J].

Bailey, WF ;

Jiang, XL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2596-2597

[7] Protecting group controlled stereoselective alkylation of asymmetrized bis(hydroxymethyl)propanoates (BHYMP*) [J].

Banfi, L ;

Guanti, G .

TETRAHEDRON-ASYMMETRY, 1999, 10 (03) :439-447

[8] Tandem radical and non-radical reactions mediated with thiols - a new method of cleavage of allylic amines [J].

Bertrand, MP ;

Escoubet, S ;

Gastaldi, S ;

Timokhin, VI .

CHEMICAL COMMUNICATIONS, 2002, (03) :216-217

[9] Importance of the thiomorpholine introduction in new pyrrole derivatives as antimycobacterial agents analogues of BM 212 [J].

Biava, M ;

Porretta, GC ;

Deidda, D ;

Pompei, R ;

Tafi, A ;

Manetti, F .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (04) :515-520

[10] Small tripeptide surrogates with low nanomolar affinity as potent inhibitors of the botulinum neurotoxin B metallo-proteolytic activity [J].

Blommaert, A ;

Turcaud, S ;

Anne, C ;

Roques, BP .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (11) :3055-3062

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