Synthesis of Enantiopure Oxygen- and Nitrogen-Containing Heterocycles by Diastereoselective Ring-Closing Metathesis Reaction in Perhydro-1,3-benzoxazine Derivatives

被引：2

作者：

Gutierrez-Loriente, Agustin ^{[1
,2
]}

Martin-Alvarez, Jose M. ^{[1
,3
]}

Prieto, Elena ^{[1
,2
]}

Andres, Celia ^{[1
,2
]}

Nieto, Javier ^{[1
,2
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Inst CINQUIMA, Paseo Belen 7, E-47011 Valladolid, Spain

[2] Univ Valladolid, Fac Ciencias, Dept Quim Organ, Paseo Belen 7, E-47011 Valladolid, Spain

[3] Univ Valladolid, Fac Ciencias, Dept Quim Inorgan, Paseo Belen 7, E-47011 Valladolid, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 05期

关键词：

Asymmetric synthesis; metathesis; oxygen heterocycles; nitrogen heterocycles; chiral auxiliaries; ENANTIOSELECTIVE OLEFIN METATHESIS; REARRANGEMENT METATHESIS; COMPLEXES; EFFICIENT; CONSTRUCTION; ALCOHOLS; BEARING; ETHERS;

D O I：

10.1002/adsc.201801454

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Diastereoselective ring-closing metathesis reactions on chiral trienic perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol featuring two diastereotopic olefin chains is described. The diastereochemical outcome of the cyclization appeared to be dependent on the length and position of the olefin chains in perhydro-1,3-benzoxazine, the degree of substitution of the double bonds and the ruthenium catalyst used. After separation of the diastereomers, and removal of the chiral auxiliary, enantiopure oxygen- and nitrogen-containing heterocycles were obtained.

引用

页码：1042 / 1063

页数：22

共 70 条

[1] Synthesis of enantiopure highly substituted trans-8a-hydroxydecahydroisoquinolines by sequential diastereoselective IMDA reaction and oxanorbornene nucleophilic ring opening [J].