ChemInform Abstract: Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters.

ChemInform ◽  
2016 ◽  
Vol 47 (11) ◽  
pp. no-no
Author(s):  
Zhaobin Wang ◽  
Yuk Fai Wong ◽  
Jianwei Sun
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides ◽  
Catalytic Asymmetric ◽  
Quaternary Stereocenters

Bifunctional tertiary amine-squaramide catalyzed asymmetric catalytic 1,6-conjugate addition/aromatization of para-quinone methides with oxindoles

2016 ◽  
Vol 52 (22) ◽  
pp. 4183-4186 ◽  
Author(s):  
Yu-Hua Deng ◽  
Xiang-Zhi Zhang ◽  
Ke-Yin Yu ◽  
Xu Yan ◽  
Ji-Yuan Du ◽  
...  
Keyword(s):  
Tertiary Amine ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Asymmetric Catalytic ◽  
Quaternary Stereocenters

A novel organocatalytic enantioselective 1,6-addition of p-QMs has been developed to access diarylmethine-functionalized oxindoles bearing vicinal tertiary and quaternary stereocenters.

Catalytic asymmetric 1,6-conjugate addition of in situ generated para-quinone methides with tritylthiol

2018 ◽  
Vol 5 (11) ◽  
pp. 1820-1824 ◽  
Author(s):  
Ya-Jing Fan ◽  
Lei Zhou ◽  
Shen Li
Keyword(s):  
Phase Transfer ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Catalytic Asymmetric

An asymmetric phase-transfer catalyzed 1,6-conjugate addition of in situ generated para-quinone methides with tritylthiol has been developed.

Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides

2018 ◽  
Vol 20 (10) ◽  
pp. 3070-3073 ◽  
Author(s):  
Zhongdong Sun ◽  
Bo Sun ◽  
Naoya Kumagai ◽  
Masakatsu Shibasaki
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides ◽  
Catalytic Asymmetric

scholarly journals Construction of all-carbon quaternary stereocenters by catalytic asymmetric conjugate addition to cyclic enones in natural product synthesis

2020 ◽  
Vol 7 (22) ◽  
pp. 3815-3841
Author(s):  
Zhuo Wang
Keyword(s):  
Natural Product ◽  
Conjugate Addition ◽  
Natural Product Synthesis ◽  
Cyclic Enones ◽  
Catalytic Asymmetric ◽  
Quaternary Stereocenters

This review discusses the construction of all-carbon quaternary stereocenters using catalytic asymmetric conjugate addition and its application in natural product synthesis.

scholarly journals Diastereodivergent chiral aldehyde catalysis for asymmetric 1,6-conjugated addition and Mannich reactions

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Wei Wen ◽  
Ming-Jing Luo ◽  
Yi Yuan ◽  
Jian-Hua Liu ◽  
Zhu-Lian Wu ◽  
...  
Keyword(s):  
Amino Acids ◽  
Dft Calculations ◽  
Mannich Reaction ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Mannich Reactions ◽  
Asymmetric Transformations ◽  
Reaction Models ◽  
Catalytic Asymmetric ◽  
High Yields

Abstract Chiral aldehyde catalysis is a burgeoning strategy for the catalytic asymmetric α-functionalization of aminomethyl compounds. However, the reaction types are limited and to date include no examples of stereodivergent catalysis. In this work, we disclose two chiral aldehyde-catalysed diastereodivergent reactions: a 1,6-conjugate addition of amino acids to para-quinone methides and a bio-inspired Mannich reaction of pyridinylmethanamines and imines. Both the syn- and anti-products of these two reactions can be obtained in moderate to high yields, diastereo- and enantioselectivities. Four potential reaction models produced by DFT calculations are proposed to explain the observed stereoselective control. Our work shows that chiral aldehyde catalysis based on a reversible imine formation principle is applicable for the α-functionalization of both amino acids and aryl methylamines, and holds potential to promote a range of asymmetric transformations diastereoselectively.

Copper-catalyzed 1,6-conjugate addition of para-quinone methides with diborylmethane

2021 ◽  
Author(s):  
Xin Li ◽  
Guoliang Gao ◽  
Songtao He ◽  
Qiuling Song
Keyword(s):  
Catalytic System ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
High Yields

Presented herein is the first 1,6-conjugate addition of diborylmethane, which is promoted by a simple and inexpensive copper catalytic system. This method features high yields, good selectivities and broad functional...

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