Camphor Derivatives in Asymmetric Cycloadditions and Rearrangements

被引：16

作者：

Langlois, Yves ^{[1
]}

Kouklovsky, Cyrille ^{[1
]}

机构：

[1] Univ Paris 11, Lab Chim Procedes & Subst Nat, ICMMO, UMR 8182, F-91405 Orsay, France

来源：

SYNLETT | 2009年 / 19期

关键词：

cycloadditions; Diels-Alder reactions; chiral auxiliaries; rearrangements; asymmetric catalysis; OXAZOLINE-N-OXIDES; MEDIATED 2+3 CYCLOADDITIONS; DIELS-ALDER REACTIONS; ALPHA; BETA-UNSATURATED OXAZOLINES; 1,3-DIPOLAR CYCLOADDITION; NITRONES; NITROALKENES; DIENOPHILE; CATALYSIS; ALDEHYDES;

D O I：

10.1055/s-0029-1218302

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Camphor-derived alpha,beta-unsaturated oxazolines and oxazoline N-oxides are, respectively, Useful dienophiles and dipolarophiles in [2+4] and [2+3] diastereoselective cycloadditions. The scope and limitations of these two reactions as well as their synthetic applications in the synthesis of various natural products are discussed. The Account also covers sigma-[2,3] rearrangement of oxazoline N-oxide, which gives a new insight into the mechanism of this type of reaction. Finally, recent developments in Diels-Alder organocatalyzed cycloaddition with camphor-derived sulfonylhydrazines are also discussed.

引用

页码：3065 / 3081

页数：17

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