Total synthesis of enantiopure (+)-γ-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation

被引：70

作者：

Chapsal, BD ^{[1
]}

Ojima, I ^{[1
]}

机构：

[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 07期

关键词：

D O I：

10.1021/ol060181v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient short total synthesis of (+)-gamma-lycorane (> 99% ee, 41% overall yield) was achieved by using the asymmetric allylic alkylation in the key step catalyzed by palladium complexes with novel chiral biphenol-based monodentate phosphoramidite ligands.

引用

页码：1395 / 1398

页数：4

共 26 条

[11] Effects of catalyst activation and ligand steric properties on the enantioselective allylation of amines and phenoxides [J].

Leitner, A ;

Shu, CT ;

Hartwig, JF .

ORGANIC LETTERS, 2005, 7 (06) :1093-1096

[12] Kinetic study of various phosphoramidite ligands in the iridium-catalyzed allylic substitution [J].

Polet, D ;

Alexakis, A .

ORGANIC LETTERS, 2005, 7 (08) :1621-1624

[13] An efficient palladium mediated synthesis of (±)-γ-lycorane [J].

Shao, ZH ;

Chen, JB ;

Huang, R ;

Wang, CY ;

Li, L ;

Zhang, HB .

SYNLETT, 2003, (14) :2228-2230

[14]

SHAO ZH, 2004, HECHENG HUAXUE, V12, P111

[15] Carbocycles via enantioselective inter- and intramolecular iridium-catalysed allylic alkylations [J].

Streiff, S ;

Welter, C ;

Schelwies, M ;

Lipowsky, G ;

Miller, N ;

Helmchen, G .

CHEMICAL COMMUNICATIONS, 2005, (23) :2957-2959

[16] Iridium complex-catalyzed highly selective organic synthesis [J].

Takeuchi, R .

SYNLETT, 2002, (12) :1954-1965

[17]

Trost B.M., 2000, CATALYTIC ASYMMETRIC

[18] Asymmetric transition metal-catalyzed allylic alkylations [J].

Trost, BM ;

VanVranken, DL .

CHEMICAL REVIEWS, 1996, 96 (01) :395-422

[19] A MODULAR APPROACH FOR LIGAND DESIGN FOR ASYMMETRIC ALLYLIC ALKYLATIONS VIA ENANTIOSELECTIVE PALLADIUM-CATALYZED IONIZATIONS [J].

TROST, BM ;

VANVRANKEN, DL ;

BINGEL, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9327-9343

[20] Regio- and enantioselective allylic alkylation of an unsymmetrical substrate: A working model [J].

Trost, BM ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (19) :4545-4554

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