Kinetic resolution of racemic α-hydroxyphosphonates by asymmetric esterification using achiral carboxylic acids with pivalic anhydride and a chiral acyl-transfer catalyst

被引：28

作者：

Shiina, Isamu ^{[1
]}

Ono, Keisuke ^{[1
]}

Nakahara, Takayoshi ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 91期

关键词：

ALCOHOLS; INHIBITORS; HYDROXYALKANEPHOSPHONATES; ANALOGS; PHOSPHONATES;

D O I：

10.1039/c3cc44293d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A practical protocol is developed to directly provide chiral alpha-acyloxyphosphonates and alpha-hydroxyphosphonates from (+/-)-alpha-hydroxyphosphonates utilizing the transacylation process to generate the mixed anhydrides from acid components and pivalic anhydride in the presence of organocatalysts (s-value = 33-518).

引用

页码：10700 / 10702

页数：3

共 48 条

[41] Parallel kinetic resolution of racemic 1-phenylethanol using quasi-enantiomeric combinations of carboxylic acids mediated by N,N′-dicyclohexylcarbodiimide and 3,5-lutidine
Al Shaye, Najla
Boa, Andrew N.
Coulbeck, Elliot
Eames, Jason
TETRAHEDRON LETTERS, 2008, 49 (31) : 4661 - 4665
[42] Kinetic resolution of racemic tertiary allylic alcohols through SN2′ reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system
Kayal, Satavisha
Kikuchi, Jun
Shinagawa, Naoya
Umemiya, Shigenobu
Terada, Masahiro
CHEMICAL SCIENCE, 2022, 13 (33) : 9607 - 9613
[43] Acylative Kinetic Resolution of Racemic 2,2-Dimethyl-Substituted Nitroaldol (Henry) Adducts Using a Chiral Guanidine Catalyst: (R)-(+)-N-Methylbenzoguanidine ((R)-NMBG)
Ichimura, Taiju
Kishida, Ryota
Nakata, Kenya
CHEMISTRYSELECT, 2019, 4 (32): : 9440 - 9443
[44] Dynamic kinetic resolution in the stereoselective synthesis of 4,5-diaryl cyclic sulfamidates by using chiral rhodium-catalyzed asymmetric transfer hydrogenation
Han, Juae
Kang, Soyeong
Lee, Hyeon-Kyu
CHEMICAL COMMUNICATIONS, 2011, 47 (13) : 4004 - 4006
[45] Asymmetric Synthesis of α,α-Disubstituted α-Amino Acids via Enantioselective Alkylation of Azlactones under Biphasic Conditions Using P-Spiro Chiral Tetraaminophosphonium Salts as a Phase-Transfer Catalyst
Uraguchi, Daisuke
Asai, Yoshihiro
Seto, Yuki
Ooi, Takashi
SYNLETT, 2009, (04) : 658 - 660
[46] A new cost-effective Ru-chloramphenicol base derivative catalyst for the asymmetric transfer hydrogenation/dynamic kinetic resolution of N-Boc α-amino-β-ketoesters and its application to the synthesis of the chiral core of vancomycin
Wang, Xinlong
Xu, Lingjun
Xiong, Fangjun
Wu, Yan
Chen, Fener
RSC ADVANCES, 2016, 6 (44): : 37701 - 37709
[47] OXAZOLINES .21. KINETIC RESOLUTION OF SEC-ALKYL HALIDES AND SIMULTANEOUS ASYMMETRIC SYNTHESIS OF 3-ALKYLALKANOIC ACIDS USING A CHIRAL OXAZOLINE - METHOD FOR DETERMINING ABSOLUTE-CONFIGURATIONS AND MAXIMUM OPTICAL ROTATIONS
MEYERS, AI
KAMATA, K
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (08) : 2290 - 2294
[48] Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts-stereoselective synthesis of anti-β-hydroxy-α-amino acids
Makino, Kazuishi
Goto, Takayuki
Hiroki, Yasuhiro
Hamada, Yasumasa
TETRAHEDRON-ASYMMETRY, 2008, 19 (24) : 2816 - 2828

← 1 2 3 4 5 →