Catalytic Asymmetric N-Alkylation of Indoles and Carbazoles through 1,6-Conjugate Addition of Aza-para -quinone Methides

2017 ◽  
Vol 129 (16) ◽  
pp. 4654-4658 ◽  
Author(s):  
Min Chen ◽  
Jianwei Sun
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides ◽  
Catalytic Asymmetric

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 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...

Organocatalytic cascade 1,6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes

2018 ◽  
Vol 29 (8) ◽  
pp. 1273-1276 ◽  
Author(s):  
Cong Duan ◽  
Ling Ye ◽  
Wenqin Xu ◽  
Xinying Li ◽  
Feng Chen ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides
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