Stereocontrolled solid-phase synthesis of fluorinated partially-modified retropeptides via tandem aza-Michael/enolate-protonation

被引：22

作者：

Volonterio, A

Chiva, G

Fustero, S

Piera, J

Rosello, MS

Sani, M

Zanda, M

机构：

[1] Mat & Ingn Chim G Natta Politech Milano, Dipartimento Chim, I-20131 Milan, Italy

[2] Univ Valencia, Fac Farm, Dept Quim Organ, E-46100 Burjassot, Spain

[3] CNR, Ist Chim Riconoscimento Mol, Sez A Quil, I-20131 Milan, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 37期

关键词：

D O I：

10.1016/S0040-4039(03)01787-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Acylation of Wang resin-bound L-alpha-amino acids with 2-trifluoromethyl-propenoyl chloride, followed by asymmetric tandem aza-Michael/enolate-protonation by a series Of L-alpha-amino esters and final release from the resin, afforded a representative library of partially-modified retropeptides incorporating a stereodefined trifluoroalanine surrogate. The stereocontrol can be dramatically improved (up to 15:1) by using apolar solvents like carbon tetrachloride and DABCO as base. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7019 / 7022

页数：4

共 35 条

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[22] Catalytic asymmetric solid-phase cyclopropanation [J].