Rhodium(I)-catalyzed asymmetric carbene insertion into B-H bonds: highly enantioselective access to functionalized organoboranes

Journal of the American Chemical Society
Diao ChenMing-Hua Xu

Abstract

A unique rhodium(I)-catalyzed asymmetric B-H insertion of α-diazo carbonyl compounds with easily available amine-borane adducts was achieved using a newly developed C1-symmetric chiral diene as ligand. This first Rh(I)-carbene-directed B-H insertion example represents an attractive and promising approach for synthesis of highly enantioenriched organoboron compounds, allowing for the efficient construction of α-boryl esters and ketones with excellent enantioselectivities (up to 99% ee) under exceptionally mild conditions.

References

Nov 16, 2007·Chemical Communications : Chem Comm·Heather E Burks, James P Morken

❮ Previous
Next ❯

Citations

Feb 26, 2016·Journal of the American Chemical Society·Christophe WerléAlois Fürstner
Jul 7, 2015·Organic Letters·Swapnil Nerkar, Dennis P Curran
Jul 14, 2016·Accounts of Chemical Research·Jonathan P MoerdykChristopher W Bielawski
Feb 15, 2017·Journal of the American Chemical Society·Ji-Min YangQi-Lin Zhou
Jan 5, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Dan Zhang, Wenhao Hu
Mar 2, 2017·Chemical Communications : Chem Comm·Daorui HuangJiangtao Sun
Dec 1, 2015·Chemical Communications : Chem Comm·Maciej GiedykDorota Gryko
Dec 1, 2017·Nature·S B Jennifer KanFrances H Arnold
Sep 19, 2019·Chemical Communications : Chem Comm·Yun-Shuai HuangYi-Feng Wang
Nov 23, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Paola NavaOlivier Chuzel
Dec 12, 2019·Chemical Communications : Chem Comm·Shang-Shi ZhangLuyong Zhang
Aug 28, 2015·Chemistry : a European Journal·Yun LinYu Rao
Dec 6, 2017·Chemistry : a European Journal·Thomas H AllenDennis P Curran
Mar 6, 2019·ACS Central Science·Xiongyi HuangFrances H Arnold
May 27, 2015·Inorganic Chemistry·P Veeraraghavan Ramachandran, Ameya S Kulkarni
Mar 12, 2019·Journal of the American Chemical Society·Xiaoliang Zou Senmiao Xu
Nov 26, 2020·Journal of the American Chemical Society·Ji-Min YangQi-Lin Zhou

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.