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
收藏
页码：5270 / 5279
页数：10
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