Catalytic asymmetric coupling of vinylogous species via deconjugated butenolide addition to vinylogous imines in situ generated from arylsulfonyl indoles

2021 ◽  
Author(s):  
Shu-Pei Yuan ◽  
Xia-Yan Zhang ◽  
Yun-Qing Jia ◽  
Zhen-Hua Wang ◽  
Jian-Qiang Zhao ◽  
...  
Keyword(s):  
Asymmetric Coupling ◽  
Catalytic Asymmetric

An efficient catalytic asymmetric coupling of vinylogous species was developed for the synthesis of enantioenriched sec-alkyl-3-substituted indoles containing adjacent quaternary-tertiary stereocenters in synthetically viable results.

scholarly journals Asymmetric Pd-NHC*-catalyzed coupling reactions

2012 ◽  
Vol 84 (8) ◽  
pp. 1741-1748 ◽  
Author(s):  
E. Peter Kündig ◽  
Yixia Jia ◽  
Dmitry Katayev ◽  
Masafumi Nakanishi
Keyword(s):  
High Temperature ◽  
Coupling Reactions ◽  
Structural Studies ◽  
Methylene Unit ◽  
Asymmetric Coupling ◽  
New Applications ◽  
Very High

Very high asymmetric inductions result in the Pd-catalyzed intramolecular arylation of amides to give 3,3-disubstituted oxindoles when new in situ-generated chiral N-heterocyclic carbene (NHC*) ligands are employed. Structural studies show that conformational locking to minimize allylic strain is the key to understanding the function of these ligands. New applications of these ligands in the frontier area of asymmetric coupling reactions involving C(sp3)–H bonds are detailed. Highly enantioenriched fused indolines are accessible using either preformed- or in situ-generated Pd-NHC* catalysts. Remarkably, this occurs at high temperature (140–160 °C) via excellent asymmetric recognition of an enantiotopic C–H bond in an unactivated methylene unit.

Catalytic Asymmetric Construction of Pyrroloindolines via an in Situ Generated Magnesium Catalyst

2014 ◽  
Vol 17 (2) ◽  
pp. 176-179 ◽  
Author(s):  
Linqing Wang ◽  
Dongxu Yang ◽  
Fengxia Han ◽  
Dan Li ◽  
Depeng Zhao ◽  
...  
Keyword(s):  
Catalytic Asymmetric

ChemInform Abstract: Catalytic Asymmetric Addition of Meldrum′s Acid, Malononitrile, and 1,3-Dicarbonyls to ortho-Quinone Methides Generated in situ under Basic Conditions.

ChemInform ◽  
2015 ◽  
Vol 46 (35) ◽  
pp. no-no
Author(s):  
Lorenzo Caruana ◽  
Martina Mondatori ◽  
Vasco Corti ◽  
Sara Morales ◽  
Andrea Mazzanti ◽  
...  
Keyword(s):  
Quinone Methides ◽  
Asymmetric Addition ◽  
Catalytic Asymmetric

ChemInform Abstract: Catalytic Asymmetric Epoxidation and Kinetic Resolution: Modified Procedures Including in situ Derivatization.

ChemInform ◽  
1988 ◽  
Vol 19 (1) ◽  
Author(s):  
Y. GAO ◽  
R. M. HANSON ◽  
J. M. KLUNDER ◽  
S. Y. KO ◽  
H. MASAMUNE ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Asymmetric Epoxidation ◽  
Catalytic Asymmetric ◽  
In Situ Derivatization

scholarly journals Pentanidium-Catalyzed Direct Assembly of Vicinal All-Carbon Quaternary Stereocenters through C(sp3)-C(sp3) Bond Formation

2021 ◽  
Author(s):  
Choon-Hong Tan ◽  
Xu Ban ◽  
Yifan Fan ◽  
Tuan-Khoa Kha ◽  
Richmond Lee ◽  
...  
Keyword(s):  
Bond Formation ◽  
Direct Assembly ◽  
Tertiary Carbon ◽  
Asymmetric Coupling ◽  
Catalytic Asymmetric ◽  
Quaternary Stereocenters ◽  
Straightforward Approach

Abstract The stereoselective construction of vicinal all-carbon quaternary stereocenters has long been a formidable synthetic challenge. Direct asymmetric coupling of a tertiary carbon nucleophile with a tertiary carbon electrophile is the most straightforward approach but it is sterically and energetically disfavored. Herein, we described a catalytic asymmetric substitution, where racemic tertiary bromides directly couple with racemic secondary or tertiary carbanion, creating a series of congested carbon (sp3)-carbon(sp3) bonds, including isolated all-carbon quaternary stereocenters, vicinal tertiary/all-carbon quaternary stereocenters and vicinal all-carbon quaternary stereocenters. This double stereoconvergent process, using pentanidium as catalyst, affords substituted products in good enantioselectivities and diastereoselectivities.

Catalytic Asymmetric (4+3) Cyclizations of In Situ Generated ortho ‐Quinone Methides with 2‐Indolylmethanols

2019 ◽  
Vol 131 (26) ◽  
pp. 8795-8800 ◽  
Author(s):  
Meng Sun ◽  
Chun Ma ◽  
Si‐Jia Zhou ◽  
Sai‐Fan Lou ◽  
Jian Xiao ◽  
...  
Keyword(s):  
Quinone Methides ◽  
Catalytic Asymmetric
Sign in / Sign up

Export Citation Format

Share Document