Asymmetric Synthesis of Chiral Atropisomeric Bis-Aryl Organophosphorus from Menthyl H-Phosphinate.
Chem Rec. 2016 Apr; 16(2):977-86.CR

Abstract

This review describes new methods for the synthesis of chiral monophosphine ligands with menthyl phenylphosphinate as a chiral auxiliary through asymmetric Suzuki-Miyaura cross-coupling reactions and asymmetric C-H functionalization. The chiral menthyl phenylphosphinate as a chiral auxiliary is easy to prepare and the menthyl group can easily be transformed into other functional groups, with the chiral center synchronously remaining. These methodologies provide highly efficient and practical strategies for the synthesis of novel axially chiral biaryl monophosphine oxides and their corresponding phosphines. Meanwhile, these reactions are easy to handle and exhibit wide scope for substrates with excellent diastereomeric ratios.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Ma YN

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China.

Yang SD

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Lanzhou, 730000, P. R. China.

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26991107

Citation

Ma, Yan-Na, and Shang-Dong Yang. "Asymmetric Synthesis of Chiral Atropisomeric Bis-Aryl Organophosphorus From Menthyl H-Phosphinate." Chemical Record (New York, N.Y.), vol. 16, no. 2, 2016, pp. 977-86.

Ma YN, Yang SD. Asymmetric Synthesis of Chiral Atropisomeric Bis-Aryl Organophosphorus from Menthyl H-Phosphinate. Chem Rec. 2016;16(2):977-86.

Ma, Y. N., & Yang, S. D. (2016). Asymmetric Synthesis of Chiral Atropisomeric Bis-Aryl Organophosphorus from Menthyl H-Phosphinate. Chemical Record (New York, N.Y.), 16(2), 977-86. https://doi.org/10.1002/tcr.201500242

Ma YN, Yang SD. Asymmetric Synthesis of Chiral Atropisomeric Bis-Aryl Organophosphorus From Menthyl H-Phosphinate. Chem Rec. 2016;16(2):977-86. PubMed PMID: 26991107.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Asymmetric Synthesis of Chiral Atropisomeric Bis-Aryl Organophosphorus from Menthyl H-Phosphinate. AU - Ma,Yan-Na, AU - Yang,Shang-Dong, Y1 - 2016/03/17/ PY - 2015/09/18/received PY - 2016/3/19/entrez PY - 2016/3/19/pubmed PY - 2016/3/19/medline KW - asymmetric C-H functionalization KW - asymmetric Suzuki-Miyaura cross-coupling KW - chiral auxiliaries KW - menthyl phenylphosphinate KW - phosphine ligands SP - 977 EP - 86 JF - Chemical record (New York, N.Y.) JO - Chem Rec VL - 16 IS - 2 N2 - This review describes new methods for the synthesis of chiral monophosphine ligands with menthyl phenylphosphinate as a chiral auxiliary through asymmetric Suzuki-Miyaura cross-coupling reactions and asymmetric C-H functionalization. The chiral menthyl phenylphosphinate as a chiral auxiliary is easy to prepare and the menthyl group can easily be transformed into other functional groups, with the chiral center synchronously remaining. These methodologies provide highly efficient and practical strategies for the synthesis of novel axially chiral biaryl monophosphine oxides and their corresponding phosphines. Meanwhile, these reactions are easy to handle and exhibit wide scope for substrates with excellent diastereomeric ratios. SN - 1528-0691 UR - https://www.unboundmedicine.com/medline/citation/26991107/Asymmetric_Synthesis_of_Chiral_Atropisomeric_Bis_Aryl_Organophosphorus_from_Menthyl_H_Phosphinate_ DB - PRIME DP - Unbound Medicine ER -

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Asymmetric Synthesis of Chiral Atropisomeric Bis-Aryl Organophosphorus from Menthyl H-Phosphinate.Chem Rec. 2016 Apr; 16(2):977-86.CR