Enantioselective Preparation of P-Chiral Phosphine Oxides

被引：59

作者：

Adams, Harry ^{[1
]}

Collins, Rebecca C. ^{[1
]}

Jones, Simon ^{[1
]}

Warner, Christopher J. A. ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

CATALYTIC ASYMMETRIC DEPROTONATION; KINETIC RESOLUTION; STEREOGENIC COMPOUNDS; PHOSPHORUS-COMPOUNDS; LIGANDS; BORANES; ROUTE; ORGANOCATALYSTS; DIPHOSPHINES; AUXILIARIES;

D O I：

10.1021/ol202916j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient chiral auxiliary-based strategy for the asymmetric synthesis of P-chiral phosphine oxides in >98:2 er has been developed. The methodology involves the highly stereoselective formation of P-chiral oxazolidinones that then undergo displacement with a variety of Grignard reagents to prepare the desired phosphine oxides.

引用

页码：6576 / 6579

页数：4

共 50 条

[21] An air-stable P-chiral phosphine ligand for highly enantioselective transition-metal-catalyzed reactions
1600, American Chemical Society, Columbus, United States (127):
[22] Synthesis of P-Chiral Phosphine Ligands and Their Applications in Asymmetric Catalysis
Imamoto, Tsuneo
Sugiya, Masashi
Oohara, Nobuhiko
Tamura, Ken
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2014, 72 (10) : 1084 - 1096
[23] Unprecedented base effect on the synthesis of chiral phosphinate esters: A new route to P-chiral phosphine oxides of high enantiomeric purity
Benabra, A
Alcudia, A
Khiar, N
Fernandez, I
Alcudia, F
TETRAHEDRON-ASYMMETRY, 1996, 7 (12) : 3353 - 3356
[24] Stereoselective synthesis and resolution of P-chiral phosphine chalcogenides.
Pietrusiewicz, KM
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 109 (1-4) : 573 - 576
[25] An air-stable P-chiral phosphine ligand for highly enantioselective transition-metal-catalyzed reactions
Imamoto, T
Sugita, K
Yoshida, K
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (34) : 11934 - 11935
[26] Synthesis and enantioselectivity of P-chiral phosphine ligands with akynyl groups
Imamoto, Tsuneo
Saitoh, Youichi
Koide, Aya
Ogura, Tomokazu
Yoshida, Kazuhiro
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (45) : 8636 - 8639
[27] Stereoselective preparation of functionalized tertiary P-chiral phosphine oxides by nucleophilic addition of lithiated tert-butylphenylphosphine oxide to carbonyl compounds.
Haynes, RK
Lam, WWL
Yeung, LL
TETRAHEDRON LETTERS, 1996, 37 (27) : 4729 - 4732
[28] PREPARATION OF SCALEMIC P-CHIRAL PHOSPHINES AND THEIR DERIVATIVES
PIETRUSIEWICZ, KM
ZABLOCKA, M
CHEMICAL REVIEWS, 1994, 94 (05) : 1375 - 1411
[29] Enantioselective Palladium-Catalyzed Hydrophosphinylation of Allenes with Phosphine Oxides: Access to Chiral Allylic Phosphine Oxides
Yang, Zhiping
Wang, Jun
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (52) : 27288 - 27292
[30] Construction of P-Chiral Alkenylphosphine Oxides through Highly Chemo-, Regio-, and Enantioselective Hydrophosphinylation of Alkynes
Dai, Qiang
Liu, Lu
Qian, Yanyan
Li, Wenbo
Zhang, Junliang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (46) : 20645 - 20650

← 1 2 3 4 5 →