Enantioselective Hydrogenation with Chiral Frustrated Lewis Pairs

Chen, Dianjun; Wang, Yutian; Klankermayer, Jürgen

doi:10.1002/anie.201004525

Cited by 280 publications

(130 citation statements)

References 44 publications

Supporting

Mentioning

122

Contrasting

Unclassified

Order By: Relevance

“…However, as the P/B FLPs derived from t Bu 3 P with 76 a and 76 b reacted with different reaction rates with dihydrogen, allowing a kinetic resolution. [66] Thus catalytic hydrogenation of the prochiral imine with the pure 77 a gave the S-amine Ph(Me)HC-NHPh with 48 % ee, while the other diastereoisomer 77 b resulted in R-amine as the hydrogenation product in excellent yield with 79 % ee (Scheme 29). Several other imines were also subjected to catalytic hydrogenation with the 77 b catalyst, several giving greater than 80 % ee.…”

Section: Asymmetric Hydrogenationmentioning

confidence: 96%

Frustrated Lewis Pair Chemistry: Development and Perspectives

2015

View full text Add to dashboard Cite

Frustrated Lewis pairs (FLPs) are combinations of Lewis acids and Lewis bases in solution that are deterred from strong adduct formation by steric and/or electronic factors. This opens pathways to novel cooperative reactions with added substrates. Small-molecule binding and activation by FLPs has led to the discovery of a variety of new reactions through unprecedented pathways. Hydrogen activation and subsequent manipulation in metal-free catalytic hydrogenations is a frequently observed feature of many FLPs. The current state of this young but rapidly expanding field is outlined in this Review and the future directions for its broadening sphere of impact are considered.

show abstract

Section: Asymmetric Hydrogenationmentioning

confidence: 96%

Frustrated Lewis Pair Chemistry: Development and Perspectives

2015

View full text Add to dashboard Cite

show abstract

“…Several ketimines 9 were suitable substrates for this asymmetric reaction to give the products 10 in 74-83% ee's. 15 This work represents the first highly enantioselective hydrogenation catalyzed by chiral FLPs. In 2012, Klankermayer and co-workers reported an intramolecular phosphine-borane FLP catalyst 18 derived from (1R)-(+)-camphor.…”

Section: Chiral Frustrated Lewis Pairs Catalyzed Asymmetric Hydrogenamentioning

confidence: 99%

“…Subsequently, the enantioselectivity was largely improved using novel chiral boranes 17 derived with (1R)-(+)-camphor as the starting material. 15 Reaction of (1R)-(+)-camphor with phenylmagnesium bromide gave alcohol 12. Subsequent dehydration resulted in chiral olefin 13.…”

Section: Chiral Frustrated Lewis Pairs Catalyzed Asymmetric Hydrogenamentioning

confidence: 99%

Metal-free asymmetric hydrogenation and hydrosilylation catalyzed by frustrated Lewis pairs

Feng

2014

Tetrahedron Letters

126

View full text Add to dashboard Cite

The activation of H2 for the catalytic hydrogenation of unsaturated compounds is one of the most useful reactions in both academia and chemical industry, which has long been predominated by the transition-metal catalysis. However, metal-free hydrogen activation represents a formidable challenge, and has been less developed. The recent emerging chemistry of frustrated Lewis pairs (FLPs) with a combination of sterically encumbered Lewis acids and Lewis bases provides a promising approach for metal-free hydrogenation due to their amazing abilities for the challenging H2 activation. In the past several years, the hydrogenation of a wide range of unsaturated compounds using FLP catalysts has been successfully developed. Despite of these advances, the corresponding asymmetric hydrogenation is just in its start-up step. Similar with the mode of H-H bond activation, Si-H bond can also be activated by FLPs for the hydrosilylation of ketones and imines. But its asymmetric version is also not well-solved. This paper will outline the recent important progress of metal-free catalytic asymmetric hydrogenation and hydrosilylation using FLP catalysts.

show abstract

“…for formation of chiral 3-hydroxyoxindole derivatives using chiral VAPOL calcium phosphate 42 . Regarding frustrated ion pairs, a bisfluorenyl-substituted allene may now be used instead of tris(pentafluorophenyl)borane for their generation and utilized in cleavage of disulfides 43 , while chiral examples have found application in asymmetric hydrogenation of imines 44 . An aldehyde decarbonylase catalyzes conversion of fatty aldehydes to alk(a,e)nes 45 .…”

Section: Trends and Developments In Synthetic Organic Chemistry 2011mentioning

confidence: 99%

Title Pages

2011

Theilheimer's Synthetic Methods of Organic Chemistry

View full text Add to dashboard Cite

show abstract

Enantioselective Hydrogenation with Chiral Frustrated Lewis Pairs

Cited by 280 publications

References 44 publications

Frustrated Lewis Pair Chemistry: Development and Perspectives

Frustrated Lewis Pair Chemistry: Development and Perspectives

Metal-free asymmetric hydrogenation and hydrosilylation catalyzed by frustrated Lewis pairs

Title Pages

Contact Info

Product

Resources

About