Asymmetric Synthesis of Chiral Cyclopentanes Bearing an All-Carbon Quaternary Stereocenter by Zirconium-Catalyzed Double Carboalumination

2017 ◽  
Vol 129 (38) ◽  
pp. 11660-11663 ◽  
Author(s):  
Shiqing Xu ◽  
Chuan Wang ◽  
Masato Komiyama ◽  
Yasuhiko Tomonari ◽  
Ei-ichi Negishi
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Cyclopentanes ◽  
Quaternary Stereocenter

Asymmetric Synthesis of Chiral Cyclopentanes Bearing an All-Carbon Quaternary Stereocenter by Zirconium-Catalyzed Double Carboalumination

2017 ◽  
Vol 56 (38) ◽  
pp. 11502-11505 ◽  
Author(s):  
Shiqing Xu ◽  
Chuan Wang ◽  
Masato Komiyama ◽  
Yasuhiko Tomonari ◽  
Ei-ichi Negishi
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Cyclopentanes ◽  
Quaternary Stereocenter

Asymmetric Synthesis of Indolines Bearing a Benzylic Quaternary Stereocenter through Intramolecular Arylcyanation of Alkenes

Synlett ◽  
2010 ◽  
Vol 2010 (11) ◽  
pp. 1709-1711 ◽  
Author(s):  
Yoshiaki Nakao ◽  
Tamejiro Hiyama ◽  
Jen-Chieh Hsieh ◽  
Shiro Ebata
Keyword(s):  
Asymmetric Synthesis ◽  
Quaternary Stereocenter

Asymmetric synthesis of spiro[chroman-3,3′-pyrazol] scaffolds with an all-carbon quaternary stereocenter via a oxa-Michael–Michael cascade strategy with bifunctional amine-thiourea organocatalysts

RSC Advances ◽  
2015 ◽  
Vol 5 (111) ◽  
pp. 91108-91113 ◽  
Author(s):  
Weiping Zheng ◽  
Jiayong Zhang ◽  
Shuang Liu ◽  
Chengbin Yu ◽  
Zhiwei Miao
Keyword(s):  
Asymmetric Synthesis ◽  
Cascade Reaction ◽  
Quaternary Stereocenter

The chiral spiro[chroman-3,3′-pyrazol] derivatives have been synthesized through a catalytic oxa-Michael–Michael cascade reaction of 2-hydroxynitrostyrenes with 4-alkenyl pyrazolin-3-ones in good yields with moderate to high stereoselectivities.

Asymmetric Construction of Halogenated Cyclic Quaternary Carbon Center through Enolate Activation of Aldehydes

Synlett ◽  
2018 ◽  
Vol 29 (20) ◽  
pp. 2601-2607 ◽  
Author(s):  
Jun-Long Li ◽  
Qing-Zhu Li ◽  
Yue Liu ◽  
Hai-Jun Leng
Keyword(s):  
Asymmetric Synthesis ◽  
Synthetic Methods ◽  
Quaternary Carbon ◽  
Quaternary Stereocenter

The construction of a chiral halogenated cyclic quaternary carbon center through various catalytic strategies is an emerging hot topic in the field of asymmetric synthesis. Herein, we give a summary of recently developed synthetic methods for preparing such structures. In addition, a novel enolate activation mode of aldehydes is highlighted, which provides an elegant pathway to access enantiopure heterocycles featuring a halogenated quaternary stereocenter through organocatalytic [4+2] cycloaddition.

Direct enantioselective Mannich reactions of α-azido cyclic ketones: asymmetric construction of chiral azides possessing an α-quaternary stereocenter

2020 ◽  
Vol 56 (1) ◽  
pp. 98-101 ◽  
Author(s):  
Xueqian Ye ◽  
Yongkai Pan ◽  
Xiaoyu Yang
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Synthesis ◽  
Cyclic Ketones ◽  
Mannich Reactions ◽  
Chiral Phosphoric Acid ◽  
Quaternary Stereocenter

Herein, we report the asymmetric synthesis of chiral azides possessing an α-quaternary stereocenter via chiral phosphoric acid catalysed direct enantioselective Mannich reactions of α-azido cyclic ketones with aldimines.

A Concise and Modular Three-Step Synthesis of (S)-Verapamil using an Enantioselective Rhodium-Catalyzed Allylic Alkylation Reaction

Synthesis ◽  
2020 ◽  
Vol 52 (15) ◽  
pp. 2185-2189 ◽  
Author(s):  
P. Andrew Evans ◽  
Mai-Jan Tom ◽  
Ben W. H. Turnbull
Keyword(s):  
Calcium Channel ◽  
Asymmetric Synthesis ◽  
Channel Blocker ◽  
Alkylation Reaction ◽  
Allylic Alkylation ◽  
Efficient Synthesis ◽  
Terminal Olefin ◽  
Bioactive Agents ◽  
Quaternary Stereocenter ◽  
Modular Nature

A concise and modular asymmetric synthesis of the calcium channel blocker (S)-verapamil is described. This approach employs an enantioselective rhodium-catalyzed allylic alkylation reaction between an α-isopropyl-substituted benzylic nitrile and allyl benzoate to construct the challenging acyclic quaternary stereocenter. The terminal olefin then serves as a convenient synthetic handle for a hydroamination to introduce the phenethylamine moiety, furnishing (S)-verapamil in three steps and 55% overall yield, thus providing the most efficient synthesis of this important pharmaceutical reported to date. Furthermore, given the modular nature of the synthesis, it can be readily modified to prepare structurally related bioactive agents.

ChemInform Abstract: Asymmetric Synthesis of Indolines Bearing a Benzylic Quaternary Stereocenter Through Intramolecular Arylcyanation of Alkenes.

ChemInform ◽  
2010 ◽  
Vol 41 (46) ◽  
pp. no-no
Author(s):  
Jen-Chieh Hsieh ◽  
Shiro Ebata ◽  
Yoshiaki Nakao ◽  
Tamejiro Hiyama
Keyword(s):  
Asymmetric Synthesis ◽  
Quaternary Stereocenter

Asymmetric Synthesis of Cyclopropanes with a Monofluorinated Quaternary Stereocenter

2012 ◽  
Vol 14 (19) ◽  
pp. 5130-5133 ◽  
Author(s):  
Pavel Ivashkin ◽  
Samuel Couve-Bonnaire ◽  
Philippe Jubault ◽  
Xavier Pannecoucke
Keyword(s):  
Asymmetric Synthesis ◽  
Quaternary Stereocenter

A highly efficient asymmetric synthesis of quaternary stereocenter-containing indolizidine and quinolizidine alkaloids using aldehydes, nitroalkenes, and unactivated cyclic ketimines

2014 ◽  
Vol 50 (100) ◽  
pp. 15913-15915 ◽  
Author(s):  
Yu Tan ◽  
Yong-Jian Chen ◽  
Hua Lin ◽  
Han-Lin Luan ◽  
Xing-Wen Sun ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Quinolizidine Alkaloids ◽  
One Pot ◽  
Efficient Approach ◽  
Highly Efficient ◽  
Quaternary Stereocenter

A highly efficient approach to the construction of indolizidines and quinolizidines bearing a bridged quaternary stereocenter has been established in a one-pot fashion using aldehydes, nitroalkenes, and cyclic ketimines.

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