Non-hydrogen bond catalyst-mediated diastereoselective conjugate additions of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone methides

2020 ◽  
Vol 18 (35) ◽  
pp. 6807-6811
Author(s):  
Ziyang Wang ◽  
Anqi Huang ◽  
Fang Fang ◽  
Pengfei Li ◽  
Guokai Liu ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Conjugate Additions ◽  
High Yields

An efficient DBU-catalyzed conjugate addition of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone methides has been developed, affording the valuable diarylmethanes in high yields with excellent diastereoselectivity.

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...

Rapid incorporation of difluoroacetate radical into para-quinone methides via radical 1,6-conjugate addition

2021 ◽  
Author(s):  
Xin Li ◽  
Songtao He ◽  
Qiuling Song
Keyword(s):  
Functional Groups ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
High Yields ◽  
Addition Pathway ◽  
Rapid Incorporation

Presented herein is a newly designed strategy which rapidly introduces ethyl difluoroacetate radicals through a dialkylzincs induced radical 1,6-conjugate addition pathway. Besides achieving high yields and excellent functional groups compatibility,...

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.

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

Asymmetric conjugate additions of 2-substituted benzofuran-3(2H)-ones to α,β-unsaturated ketones catalyzed by chiral copper complexes

2017 ◽  
Vol 15 (19) ◽  
pp. 4191-4198 ◽  
Author(s):  
Haojiang Wang ◽  
Yifeng Wang ◽  
Cheng Zhang ◽  
Yidong Jiang ◽  
Mingming Chu ◽  
...  
Keyword(s):  
Copper Complexes ◽  
Conjugate Addition ◽  
Conjugate Additions ◽  
Unsaturated Ketones

A highly enantioselective conjugate addition of 2-substituted benzofuran-3(2H)-ones to α,β-unsaturated ketones promoted by chiral copper complexes has been developed.

Ruthenium-catalyzed Asymmetric Dehydrative Allylic Cyclization of Chalcogen 5-Membered Heteroaromatics

Synthesis ◽  
2021 ◽  
Author(s):  
Shinji Tanaka ◽  
Shoutaro Iwase ◽  
Sena Kanda ◽  
Marie Kato ◽  
Yutaro Kiriyama ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Bond Formation ◽  
Selection Method ◽  
Allylic Alcohol ◽  
Hydrogen Bond Formation ◽  
Pyridine Carboxylic Acid ◽  
Bicyclic Compounds ◽  
Allyl Complex ◽  
Pyridine Carboxylic ◽  
High Yields

The asymmetric dehydrative intramolecular allylation reactions of furan and thiophene were performed using a cationic cyclopentadienyl-ruthenium (CpRu) complex of a chiral pyridine carboxylic acid, namely Cl-Naph-PyCOOH. Both furan and thiophene tethered with an allylic alcohol gave the corresponding bicyclic compounds in high yields and enantioselectivities using 0.1–5 mol% of catalyst. The reaction was found to proceed via a similar enantioface selection method mechanism to that previously reported by our group, which involved halogen and hydrogen bond formation, in addition to the generation of an intermediate σ-allyl complex.

scholarly journals Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with ortho-Quinone Methides

Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6751
Author(s):  
Si-Jia Liu ◽  
Man-Su Tu ◽  
Kai-Yue Liu ◽  
Jia-Yi Chen ◽  
Shao-Fei Ni ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Structural Diversity ◽  
Quinone Methides ◽  
Chiral Phosphoric Acid ◽  
Catalytic Asymmetric ◽  
High Yields ◽  
Asymmetric Cycloadditions

Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with ortho-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives.

1,6-Conjugate-Addition-Induced [2 + 1] Annulation of para-Quinone Methides and Pyrazolones: Synthesis of Bis-Spiro Compounds with Contiguous Quaternary Spiro-Centers

2019 ◽  
Vol 21 (19) ◽  
pp. 7736-7740 ◽  
Author(s):  
Someshwar B. Kale ◽  
Popat K. Jori ◽  
Thanusha Thatikonda ◽  
Rajesh G. Gonnade ◽  
Utpal Das
Keyword(s):  
Conjugate Addition ◽  
Spiro Compounds ◽  
Quinone Methides

Diastereo- and Enantioselective 1,6-Conjugate Addition of 2-Azaarylacetamides to para-Quinone Methides

2019 ◽  
Vol 21 (15) ◽  
pp. 6063-6067 ◽  
Author(s):  
Yan Wang ◽  
Kaixuan Wang ◽  
Weidi Cao ◽  
Xiaohua Liu ◽  
Xiaoming Feng
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides

scholarly journals Cover Feature: para -Quinone Methides as Acceptors in 1,6-Nucleophilic Conjugate Addition Reactions for the Synthesis of Structurally Diverse Molecules (Eur. J. Org. Chem. 18/2020)

2020 ◽  
Vol 2020 (18) ◽  
pp. 2642-2642
Author(s):  
Carolina G. S. Lima ◽  
Fernanda P. Pauli ◽  
Dora C. S. Costa ◽  
Acácio S. de Souza ◽  
Luana S. M. Forezi ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Quinone Methides
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