The Aryne [2,3] Stevens Rearrangement

被引：45

作者：

Roy, Tony ^{[1
,2
,3
]}

Thangaraj, Manikandan ^{[1
,2
,3
]}

Kaicharla, Trinadh ^{[1
,2
,3
]}

Kamath, Rupa V. ^{[1
,2
]}

Gonnade, Rajesh G.

Biju, Akkattu T. ^{[1
,2
,3
]}

机构：

[1] CSIR, Natl Chem Lab, Div Organ Chem, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[2] CSIR, Natl Chem Lab, Ctr Mat Characterizat, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[3] Acad Sci & Innovat Res AcSIR, New Delhi 110020, India

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 20期

关键词：

ALLYLIC AMMONIUM YLIDES; AMINO-ACID DERIVATIVES; EMPLOYING ARYNES; NATURAL-PRODUCTS; TERTIARY-AMINES; NITROGEN; CARBON; HETEROCYCLES; GENERATION; ALKYLATION;

D O I：

10.1021/acs.orglett.6b02809

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arynes are employed in the transition-metal-free and mild [2,3] Stevens rearrangement of tertiary allylic amines for the synthesis of functionalized homoallylic amines in moderate to good yield with a broad substrate scope. The key nitrogen ylide intermediate was generated by the N-arylation of allyl amines using arynes. Moreover, the reaction of chiral allyl amines with arynes resulted in the enantiospecific synthesis of homoallylic amines. In addition, preliminary studies on the [1,2] Stevens rearrangement is also presented.

引用

页码：5428 / 5431

页数：4

共 56 条

[1] Tandem formation and [2,3] rearrangement of methylene ammonium ylides derived from amines and the Simmons-Smith reagent [J].