Synthesis of Enantioenriched γ-Amino-α,β-unsaturated Esters Utilizing Palladium-Catalyzed Rearrangement of Allylic Carbamates for Direct Application to Formal [3+2] Cycloaddition

被引：17

作者：

Kondoh, Azusa ^{[1
]}

Kamata, Yuji ^{[2
]}

Terada, Masahiro ^{[1
,2
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Aoba Ku, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 07期

关键词：

HORNER-WADSWORTH-EMMONS; ALPHA-AMINO ALDEHYDES; ACID-DERIVATIVES; AMINATION; ALCOHOLS; HOMOLOGATION; ENTRY; BASE;

D O I：

10.1021/acs.orglett.7b00471

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of enantioenriched gamma-amino-alpha,beta-usaturated esters was developed by utilizing the palladium-catalyzed decarboxylative rearrangement of enantioenriched allylic carbamates possessing an ester moiety at the allylic position. The reaction proceeded in good yield with a high degree of chirality transfer by making use of Xantphos as a superior ligand for the catalyst. The products directly participated in the formal [3 + 2] cycloaddition reaction with tosyl isocyanate under Bronsted base catalysis to afford enantioenriched beta,gamma-diamino acid derived imidazolidin-2-ones as versatile chiral building blocks.

引用

页码：1682 / 1685

页数：4

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