Phosphoramidite-Cu(OTf)2 Complexes as Chiral Catalysts for 1,3-Dipolar Cycloaddition of lminoesters and Nitroalkenes

被引：62

作者：

Castello, Luis M. ^{[1
,2
]}

Najera, Carmen ^{[1
,2
]}

Sansano, Jose M. ^{[1
,2
]}

Larranaga, Olatz ^{[3
]}

de Cozar, Abel ^{[3
,4
]}

Cossio, Fernando P. ^{[3
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

[2] Univ Alicante, Fac Ciencias, ISO, Alicante 03080, Spain

[3] Univ Basque Country, Fac Quim, Dept Quim Organ 1, E-20018 San Sebastian, Spain

[4] Basque Fdn Sci, IKERBASQUE, Bilbao 48011, Spain

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 12期

关键词：

SELECTIVE 3+2 CYCLOADDITION; AZOMETHINE YLIDES; CONJUGATE ADDITION; ALKENES;

D O I：

10.1021/ol4006618

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral complexes formed by phosphoramidites such as (S-a,R,R)-9 and Cu(OTf)(2) are excellent catalysts for the general 1,3-dipolar cycloaddition between azomethine ylides and nitroalkenes affording the corresponding tetrasubstituted proline esters mainly as exo-cycloadducts in high er at room temperature. The exo-cycloadducts can be obtained in enantiomerically pure form just after simple recrystallization. DFT calculations support the stereochemical results.

引用

页码：2902 / 2905

页数：4

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