1,2-cyclic sulfamidates as versatile precursors to thiomorpholines and piperazines

被引：62

作者：

Williams, AJ

Chakthong, S

Gray, D

Lawrence, RM

Gallagher, T

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] GlaxoSmithKline, Med Res Ctr, Chem Dev, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 06期

关键词：

D O I：

10.1021/ol027418h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Graphics 1,2-Cyclic sulfamidates undergo regiospecific nucleophilic displacement with either methyl thioglycolate or a-amino esters, followed by lactamization (thermal, base-mediated, or cyanide-catalyzed), to give thiomorpholin-3-ones and piperazin-2-ones.

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页码：811 / 814

页数：4

相关论文

共 48 条

[1] Use of cyclic sulfamidates derived from D-allosamine in nucleophilic displacements: Scope and limitations [J].

Aguilera, B ;

FernandezMayoralas, A ;

Jaramillo, C .

TETRAHEDRON, 1997, 53 (16) :5863-5876

[2] Synthesis of a thio-analogue of Lewis X by regioselective opening of cyclic sulfamidates [J].

Aguilera, B ;

Fernández-Mayoralas, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2719-2723

[3] Nucleophilic displacements on a cyclic sulfamidate derived from allosamine: Application to the synthesis of thiooligosaccharides [J].

Aguilera, B ;

FernandezMayoralas, A .

CHEMICAL COMMUNICATIONS, 1996, (02) :127-128

[4] N-(9-(9-phenylfluorenyl))homoserine-derived cyclic sulfamidates:: Novel chiral educts for the synthesis of enantiopure γ-substituted α-amino acids [J].

Atfani, M ;

Wei, L ;

Lubell, WD .

ORGANIC LETTERS, 2001, 3 (19) :2965-2968

[5] CYCLIC SULPHAMIDATES - NEW SYNTHETIC PRECURSORS FOR BETA-FUNCTIONALIZED ALPHA-AMINO-ACIDS [J].

BALDWIN, JE ;

SPIVEY, AC ;

SCHOFIELD, CJ .

TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :881-884

[6] Preparation of substituted piperazinones via tandem reductive amination-(N,N′-acyl transfer)-cyclization [J].

Beshore, DC ;

Dinsmore, CJ .

ORGANIC LETTERS, 2002, 4 (07) :1201-1204

[7] Generation of unnatural α,α-disubstituted amino acid derivatives from cyclic sulfamidates [J].

Boulton, LT ;

Stock, HT ;

Raphy, J ;

Horwell, DC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (11) :1421-1429

[8] Cyclic sulfites and cyclic sulfates in organic synthesis [J].

Byun, HS ;

He, LL ;

Bittman, R .

TETRAHEDRON, 2000, 56 (37) :7051-7091

[9] Application of serine- and threonine-derived cyclic sulfamidates for the preparation of S-linked glycosyl amino acids in solution- and solid-phase peptide synthesis [J].

Cohen, SB ;

Halcomb, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) :2534-2543

[10] Synthesis of S-linked glycosyl amino acids in aqueous solution with unprotected carbohydrates [J].

Cohen, SB ;

Halcomb, RL .

ORGANIC LETTERS, 2001, 3 (03) :405-407

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