+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

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

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

Journal of the American Chemical Society 137(16): 5268-5271

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.

Please choose payment method:

(PDF emailed within 0-6 h: $19.90)

Accession: 058773492

Download citation: RISBibTeXText

PMID: 25726987

DOI: 10.1021/jacs.5b00892

Related references

Rhodium(II)- or Copper(I)-Catalyzed Formal Intramolecular Carbene Insertion into Vinylic C(sp 2 )-H Bonds: Access to Substituted 1H-Indenes. Angewandte Chemie 56(50): 16013-16017, 2017

Highly enantioselective intermolecular carbene insertion to C-H and Si-H bonds catalyzed by a chiral iridium(III) complex of a D4-symmetric Halterman porphyrin ligand. Chemical Communications 48(36): 4299-4301, 2012

Rhodium(I)-Catalyzed Highly Enantioselective Insertion of Carbenoid into Si-H: Efficient Access to Functional Chiral Silanes. Journal of the American Chemical Society 138(5): 1498-1501, 2016

Enantioselective Palladium-Catalyzed Carbene Insertion into the N-H Bonds of Aromatic Heterocycles. Angewandte Chemie 56(15): 4156-4159, 2017

Highly enantioselective rhodium(I)-catalyzed activation of enantiotopic cyclobutanone C-C bonds. Angewandte Chemie 53(11): 3001-3005, 2014

Highly enantioselective cycloisomerization of enynes catalyzed by rhodium for the preparation of functionalized lactams. Angewandte Chemie 41(23): 4526-4529, 2002

Copper-catalyzed highly enantioselective carbenoid insertion into Si-H bonds. Angewandte Chemie 47(44): 8496-8498, 2008

Highly enantioselective reductive cyclization of acetylenic aldehydes via rhodium catalyzed asymmetric hydrogenation. Journal of the American Chemical Society 128(33): 10674-5, 2006

Chiral phosphine-phosphite ligands in the highly enantioselective rhodium-catalyzed asymmetric hydrogenation. Journal of Organic Chemistry 66(23): 7626-7631, 2001

Gold-catalyzed highly regio- and enantioselective vinylcarbene insertion into O-H bonds of 2-pyridones. Chemical Communications 53(22): 3197-3200, 2017

Copper-Catalyzed Formal Carbene Migratory Insertion into Internal Olefinic C═C Bonds with N-Tosylhydrazones To Access Iminofuran and 2(3H)-Furanone Derivatives. Organic Letters 19(13): 3660-3663, 2017

Rhodium-catalyzed asymmetric hydroformylation of N-allylamides: highly enantioselective approach to beta2-amino aldehydes. Angewandte Chemie 49(24): 4047-4050, 2010

Highly enantioselective and efficient synthesis of flavanones including pinostrobin through the rhodium-catalyzed asymmetric 1,4-addition. Organic Letters 13(8): 2022-2025, 2011

Highly enantioselective insertion of carbenoids into N-H bonds catalyzed by copper(I) complexes of binol derivatives. Angewandte Chemie 49(28): 4763-4766, 2010

Asymmetric Synthesis of Highly Functionalized Cyclopentanes by a Rhodium- and Scandium-Catalyzed Five-Step Domino Sequence. Chemical Science 2(12): 2378-2382, 2011