Enantioselective reduction of N-alkyl ketimines with frustrated Lewis pair catalysis using chiral borenium ions

被引：27

作者：

Mercea, Dan M. ^{[1
]}

Howlett, Michael G. ^{[1
]}

Piascik, Adam D. ^{[1
]}

Scott, Daniel J. ^{[1
]}

Steven, Alan ^{[2
]}

Ashley, Andrew E. ^{[1
]}

Fuchter, Matthew J. ^{[1
]}

机构：

[1] Imperial Coll London, Mol Sci Res Hub, Dept Chem, White City Campus,Wood Lane, London W12 0BZ, England

[2] AstraZeneca PT&D, Charter Way, Macclesfield SK10 2NA, Cheshire, England

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 49期

基金：

英国工程与自然科学研究理事会;

关键词：

HETEROCYCLIC CARBENE LIGANDS; H BOND ACTIVATION; ASYMMETRIC HYDROGENATION; B(C6F5)(3)-CATALYZED HYDROSILATION; BORANE; IMINES; ACIDITY; HYDROSILYLATION; POLYMERIZATION; BORYLATION;

D O I：

10.1039/c9cc02900a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective reduction of ketimines was demonstrated using chiral N-heterocyclic carbene (NHC)-stabilised borenium ions in frustrated Lewis pair catalysis. High levels of enantioselectivity were achieved for substrates featuring secondary N-alkyl substituents. Comparative reactivity and mechanistic studies identify key determinants required to achieve useful enantioselectivity and represent a step forward in the further development of enantioselective FLP methodologies.

引用

页码：7077 / 7080

页数：4

共 44 条

[1] A Highly Enantioselective Organocatalytic Method for Reduction of Aromatic N-Alkyl Ketimines
Wang, Chao
Wu, Xinjun
Zhou, Li
Sun, Jian
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (29) : 8789 - 8792
[2] Chiral Lewis Base Catalyzed Highly Enantioselective Reduction of N-Alkyl β-Enamino Esters with Trichlorosilane and Water
Wu, Xinjun
Li, Yang
Wang, Chao
Zhou, Li
Lu, Xiaoxia
Sun, Jian
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (10) : 2846 - 2848
[3] Frustrated Lewis Pair-Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis
Sieland, Benedikt
Hoppe, Axel
Stepen, Arne J.
Paradies, Jan
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (18) : 3143 - 3148
[4] Enantioselective cooperative catalysis within frustrated lewis pair complexes
Wasa M.
Yesilcimen A.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2021, 79 (11): : 1065 - 1072
[5] Enantioselective Cooperative Catalysis within Frustrated Lewis Pair Complexes
Wasa, Masayuki
Yesilcimen, Ahmet
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2021, 79 (11) : 1065 - 1072
[6] Chiral Lewis base promoted trichlorosilane reduction of ketimines. An enantioselective organocatalytic synthesis of chiral amines
Guizzetti, Stefania
Benaglia, Maurizio
Cozzi, Franco
Annunziata, Rita
TETRAHEDRON, 2009, 65 (32) : 6354 - 6363
[7] Chiral N-formyl amino alcohol as Lewis basic organocatalyst for enantioselective hydrosilylation of ketimines
Wang ZhouYu
Zhou Li
Lu XiaoXia
Sun Jian
CHINESE SCIENCE BULLETIN, 2010, 55 (17): : 1726 - 1728
[8] Chiral N-formyl amino alcohol as Lewis basic organocatalyst for enantioselective hydrosilylation of ketimines
WANG ZhouYu1
Science Bulletin, 2010, (17) : 1726 - 1728
[9] 1,1′-Binaphthyldiamine-Based Lewis Bases as Readily Available and Efficient Organocatalysts for the Reduction of N-Aryl and N-Alkyl Ketimines
Guizzetti, Stefania
Benaglia, Maurizio
Celentano, Giuseppe
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (22) : 3683 - 3687
[10] Hydrogenation of Secondary Amides using Phosphane Oxide and Frustrated Lewis Pair Catalysis
Koering, Laura
Sitte, Nikolai A.
Bursch, Markus
Grimme, Stefan
Paradies, Jan
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (57) : 14179 - 14183

← 1 2 3 4 5 →