A facile and highly diastereoselective synthesis of carbocyclic spiro-pyrazolones via DABCO catalyzed Michael-Michael domino reaction

被引：14

作者：

Rana, Nirmal K. ^{[1
,3
]}

Shukla, Khyati ^{[2
]}

Mahto, Pratibha ^{[2
]}

Jha, Rupesh K. ^{[2
]}

Singh, Vinod K. ^{[1
,2
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, India

[2] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India

[3] Indian Inst Technol Jodhpur, Dept Chem, Jodhpur 342037, Rajasthan, India

来源：

TETRAHEDRON | 2018年 / 74卷 / 38期

关键词：

Domino; Michael-Michael; Spiro-pyrazolones; Nitro alpha; beta-unsaturated esters; DABCO; MODULARLY DESIGNED ORGANOCATALYSTS; HYDROGEN-BONDING ORGANOCATALYSTS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; UNSATURATED PYRAZOLONES; TETRASUBSTITUTED CYCLOHEXANES; STEREOGENIC CENTERS; SEQUENTIAL REACTION; CONJUGATE ADDITION; CASCADE REACTIONS;

D O I：

10.1016/j.tet.2018.02.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient domino Michael-Michael reaction of omega- and delta-nitro alpha,beta-unsaturated esters with alkylide-nepyrazolones has been accomplished using DABCO as the organocatalyst under mild reaction conditions. Under the present organocatalytic method, a wide range of carbocyclic spiro-pyrazolones with three tertiary stereogenic centers and a quaternary stereocenter has been prepared in high yields and excellent diastereoselectivities. An ester and nitro groups present in the spiro-pyrazolones have been utilized for further structural transformations. (C) 2018 Published by Elsevier Ltd.

引用

页码：5270 / 5279

页数：10

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