Stereospecific construction of substituted piperidines. Synthesis of (-)-paroxetine and (+)-laccarin

被引：51

作者：

Bower, John F.

Riis-Johannessen, Thomas

Szeto, Peter

Whitehead, Andrew J.

Gallagher, Timothy

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：

CHEMICAL COMMUNICATIONS | 2007年 / 07期

关键词：

D O I：

10.1039/b617260a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Short and efficient enantioselective syntheses of (-)-paroxetine and (+)-laccarin are described based on the highly stereospecific cleavage of C(3)-substituted 1,3-cyclic sulfamidates.

引用

页码：728 / 730

页数：3

共 38 条

[1] Synthesis of enantiopure 3,4-disubstituted piperidines. An asymmetric synthesis of (+)-paroxetine [J].

Amat, M ;

Hidalgo, J ;

Bosch, J .

TETRAHEDRON-ASYMMETRY, 1996, 7 (06) :1591-1594

[2] Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine [J].

Amat, M ;

Bosch, J ;

Hidalgo, J ;

Cantó, M ;

Pérez, M ;

Llor, N ;

Molins, E ;

Miravitlles, C ;

Orozco, M ;

Luque, J .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3074-3084

[3]

Baker SR, 1998, TETRAHEDRON LETT, V39, P331

[4]

BARNES RDB, 1986, Patent No. 0223403

[5] Reactivity of cyclic sulfamidates towards sulfur-stabilised enolates. Stereocontrolled synthesis of functionalised lactams [J].

Bower, JF ;

Chakthong, S ;

Svenda, J ;

Williams, AJ ;

Lawrence, RM ;

Szeto, P ;

Gallagher, T .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (10) :1868-1877

[6] Cyclic sulfamidates as lactam precursors. An efficient asymmetric synthesis of (-)-aphanorphine [J].

Bower, JF ;

Szeto, P ;

Gallagher, T .

CHEMICAL COMMUNICATIONS, 2005, (46) :5793-5795

[7] Cyclic sulfamidates as vehicles for the synthesis of substituted lactams [J].

Bower, JF ;

Svenda, J ;

Williams, AJ ;

Charmant, JPH ;

Lawrence, RM ;

Szeto, P ;

Gallagher, T .

ORGANIC LETTERS, 2004, 6 (25) :4727-4730

[8] Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones [J].

Brandau, Sven ;

Landa, Aitor ;

Franzen, Johan ;

Marigo, Mauro ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4305-4309

[9] Synthesis of piperidines [J].

Buffat, MGP .

TETRAHEDRON, 2004, 60 (08) :1701-1729

[10] From peptides to non-peptide peptidomimetics: Design and synthesis of new piperidine inhibitors of aspartic peptidases [J].

Bursavich, MG ;

West, CW ;

Rich, DH .

ORGANIC LETTERS, 2001, 3 (15) :2317-2320

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