A Strategy Enabling Enantioselective Direct Conjugate Addition of Inert Aryl Methane Nucleophiles to Enals with a Chiral Amine Catalyst under Mild Conditions

2013 ◽  
Vol 19 (28) ◽  
pp. 9147-9150 ◽  
Author(s):  
Tengfei Li ◽  
Jin Zhu ◽  
Deyan Wu ◽  
Xiangmin Li ◽  
Sinan Wang ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Chiral Amine ◽  
Mild Conditions

Regio- and Stereoselective Conjugate Addition of Aldehydes to β-Tosyl Enones under the Catalysis of a Binaphthyl-Modified Chiral Amine

2015 ◽  
Vol 54 (29) ◽  
pp. 8462-8465 ◽  
Author(s):  
Taichi Kano ◽  
Hisashi Sugimoto ◽  
Hiroki Maruyama ◽  
Keiji Maruoka
Keyword(s):  
Conjugate Addition ◽  
Chiral Amine

scholarly journals Organocatalytic enantioselective dearomatization of thiophenes by 1,10-conjugate addition of indole imine methides

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xingguang Li ◽  
Meng Duan ◽  
Peiyuan Yu ◽  
K. N. Houk ◽  
Jianwei Sun
Keyword(s):  
Hydrogen Bonding ◽  
Phosphoric Acid ◽  
Nucleophilic Addition ◽  
Acid Catalysis ◽  
Conjugate Addition ◽  
Mild Conditions ◽  
Rapid Construction ◽  
Chiral Phosphoric Acid ◽  
Cyclic Molecules ◽  
Selectivity Control

AbstractCatalytic asymmetric dearomatization (CADA) is a powerful tool for the rapid construction of diverse chiral cyclic molecules from cheap and easily available arenes. This work reports an organocatalytic enantioselective dearomatization of substituted thiophenes in the context of a rare remote asymmetric 1,10-conjugate addition. By suitable stabilization of the thiophenyl carbocation with an indole motif in the form of indole imine methide, excellent remote chemo-, regio-, and stereocontrol in the nucleophilic addition can be achieved with chiral phosphoric acid catalysis under mild conditions. This protocol can be successfully extended to the asymmetric dearomatization of other heteroarenes including selenophenes and furans. Control experiments and DFT calculations demonstrate a possible pathway in which hydrogen bonding plays an important role in selectivity control.

Synthesis of Malononitrile-Substituted Diarylmethines via 1,6-Addition of Masked Acyl Cyanides to para-Quinone Methides

Synthesis ◽  
2017 ◽  
Vol 50 (04) ◽  
pp. 872-880 ◽  
Author(s):  
Dieter Enders ◽  
Kun Zhao ◽  
Ying Zhi ◽  
Ai Wang
Keyword(s):  
Bioactive Compounds ◽  
Efficient Method ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Mild Conditions ◽  
Synthetic Utility

An efficient method for the synthesis of malononitrile-substituted­ diarylmethines through 1,6-conjugate addition of para-quinone­ methides with masked acyl cyanide (MAC) reagents has been developed. Under mild conditions, the scalable reaction occurs in good to excellent yields providing a straightforward access to a series of malononitrile-substituted diarylmethines. The synthetic utility of this protocol has been demonstrated in the synthesis of bioactive compounds.

Chiral amine-catalyzed asymmetric conjugate addition of aldehydes to α-phenylselenoenones as formal Z-allylating agents

2018 ◽  
Vol 54 (2) ◽  
pp. 176-179 ◽  
Author(s):  
Taichi Kano ◽  
Hiroki Maruyama ◽  
Chihiro Homma ◽  
Keiji Maruoka
Keyword(s):  
Conjugate Addition ◽  
Chiral Amine

α-Selenoenones could be employed as Z-allyl precursors in the chiral amine-catalyzed asymmetric conjugate addition of aldehydes.

Diastereo- and Enantioselective Conjugate Addition of 3-Substituted Oxindoles to Nitroolefins Catalyzed by a Chiral Ni(OAc)2-Diamine Complex under Mild Conditions

2011 ◽  
Vol 13 (19) ◽  
pp. 5064-5067 ◽  
Author(s):  
Yan-Yan Han ◽  
Zhi-Jun Wu ◽  
Wen-Bing Chen ◽  
Xi-Lin Du ◽  
Xiao-Mei Zhang ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Mild Conditions

scholarly journals Cs2CO3/[bmim]Br as an Efficient, Green, and Reusable Catalytic System for the Synthesis of N-Alkyl Derivatives of Phthalimide under Mild Conditions

2008 ◽  
Vol 2008 ◽  
pp. 1-4 ◽  
Author(s):  
Alireza Hasaninejad ◽  
Abdolkarim Zare ◽  
Ahmad Reza Moosavi-Zare ◽  
Fatemeh Khedri ◽  
Rahimeh Rahimi ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Catalytic System ◽  
Reaction Times ◽  
Catalytic Amount ◽  
Conjugate Addition ◽  
Reaction Conditions ◽  
Mild Conditions ◽  
Alkyl Derivatives ◽  
High Yields ◽  
Derivatives Of

Aza-conjugate addition of phthalimide to α,β-unsaturated esters efficiently achieves in the presence of catalytic amount of Cs2CO3 and ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim]Br) under mild reaction conditions (70°C) to afford N-alkyl phthalimides in high yields and relatively short reaction times.

scholarly journals Stereoselective synthesis of perillaldehyde-based chiral β-amino acid derivatives through conjugate addition of lithium amides

2014 ◽  
Vol 10 ◽  
pp. 2738-2742 ◽  
Author(s):  
Zsolt Szakonyi ◽  
Reijo Sillanpää ◽  
Ferenc Fülöp
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Minor Component ◽  
Conjugate Addition ◽  
Building Blocks ◽  
Major Product ◽  
Amino Ester ◽  
Chiral Amine ◽  
Amino Esters ◽  
Lithium Amides

The Michael addition of dibenzylamine to (+)-tert-butyl perillate (3) and to (+)-tert-butyl phellandrate (6), derived from (S)-(−)-perillaldehyde (1), resulted in diastereomeric β-amino esters 7A–D in a moderately stereospecific reaction in a ratio of 76:17:6:1. After separation of the diastereoisomers, the major product, cis isomer 7A, was quantitatively isomerized to the minor component, trans-amino ester 7D. All four isomers were transformed to the corresponding β-amino acids 10A–D, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles in three steps. The steric effects of the isopropyl group at position 4 and of the α-methyl substituent of (R)-N-benzyl-N-α-methylbenzylamine on the reactivity were also studied and, upon application of a chiral amine, excellent stereoselectivity of the conjugate addition was observed. Amino ester 11 was obtained as a single product and transformed to the corresponding amino acids 10A and 10D in good yields on the gram scale.

Diastereo- and Enantioselective Conjugate Addition of α-Ketoesters to Nitroalkenes Catalyzed by a Chiral Ni(OAc)2Complex under Mild Conditions

2010 ◽  
Vol 132 (12) ◽  
pp. 4036-4037 ◽  
Author(s):  
Ayako Nakamura ◽  
Sylvain Lectard ◽  
Daisuke Hashizume ◽  
Yoshitaka Hamashima ◽  
Mikiko Sodeoka
Keyword(s):  
Conjugate Addition ◽  
Mild Conditions
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