Efficient chiral monophosphorus ligands for asymmetric suzuki-miyaura coupling reactions.
Summary of "Efficient chiral monophosphorus ligands for asymmetric suzuki-miyaura coupling reactions."
A series of novel P-chiral monophosphorus ligands exhibit efficiency in asymmetric Suzuki-Miyaura coupling reactions, enabling the construction of an array of chiral biaryl products in high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. The carbonyl-benzooxazolidinone moiety in these chiral biaryl products allows facile derivatization for further synthetic applications. A computational study has revealed that a π-π interaction between the two coupling partners can enhance the enantioselectivity of the coupling reaction.
Affiliation
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China, and Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridge
Journal Details
This article was published in the following journal.
Name: Organic letters
ISSN: 1523-7052
Pages: 2258-61
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22497425
- DOI: http://dx.doi.org/10.1021/ol300659d
Medical and Biotech [MESH] Definitions
Peptoids
Polymers of N-SUBSTITUTED GLYCINES containing chiral centers at the a-position of their side chains. These oligomers lack HYDROGEN BONDING donors, preventing formation of the usual intrachain hydrogen bonds but can form helices driven by the steric influence of chiral side chains.
Imidazoline Receptors
Receptors of CLONIDINE and other IMIDAZOLINES. Activity of the ligands was earlier attributed to ADRENERGIC ALPHA-2 RECEPTORS. Endogenous ligands include AGMATINE, imidazoleacetic acid ribotide, and harman.
Carbohydrate Epimerases
Enzymes that catalyze the epimerization of chiral centers within carbohydrates or their derivatives. EC 5.1.3.
Amino Acid Isomerases
Enzymes that catalyze either the racemization or epimerization of chiral centers within amino acids or derivatives. EC 5.1.1.
Nodal Signaling Ligands
Members of the transforming growth factor superfamily that play a role in pattern formation and differentiation during the pregastrulation and GASTRULATION stages of chordate development. Several nodal signaling ligands are specifically involved in the genesis of left-right asymmetry during development. The protein group is named after a critical region of the vertebrate embryo PRIMITIVE STREAK referred to as HENSEN'S NODE.
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