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Recent Advances in Asymmetric Synthesis of Р-Stereogenic Phosphorus Compounds

  • Oleg I. KolodiazhnyiEmail author
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 360)

Abstract

This chapter points out significant advances in the asymmetric synthesis of P-chiral organophosphorus compounds with many applications in stereoselective synthesis and in asymmetric catalysis, making reference to updated literature findings as well as the author’s original research. Asymmetric addition and cycloaddition reactions, oxidation, including metal catalyzed and non-metal biocatalytic methods are described, in addition to synthetic approaches via nucleophilic substitution of appropriately substituted precursors. Use of chiral organophosphorus compounds in some asymmetric transformations such as hydrogenation and alkyl/arylation reactions is also discussed.

Keywords

Asymmetric catalysis Asymmetric synthesis Biocatalysis Ephedrine P-Chiral phosphorus compounds Sparteine 

Abbreviations

Ac

Acetyl

Ad

Adamantyl

All

Allyl

Amano AH

Pseudomonas cepacia lipase

Amano AK

Pseudomonas fluorescens lipase

Amano PS

Burkholderia cepacia lipase

An

Anisyl

Bn

Benzyl

Brn

endo-Bornyl

CALB

Candida antarctica lipase (Chirazyme®L-2, Novozym 435b)

COD

Cyclooctadiene

Cp

Cyclopentadiene

CRL

Candida rugosa lipase

Cy

Cyclohexyl

DABCO

Diazabicyclooctane

DBTA

Dibenzoyltartaric acid

DBU

1,8-Diazabicyclo[5.4.0]undec-7-ene

de

Diastereoisomeric excess

DIAD

Diisopropyl azodicarboxylate

DIPAMP

Ethane-1,2-diylbis[(2-methoxyphenyl)phenylphosphane]

DIPEA

N,N-Diisopropylethylamine

DMAP

4-Dimethylaminopyridine

DME

Dimethoxyethane

DMF

N,N-Dimethylformamide

DMSO

Dimethylsulfoxide

DPPE

1,1-Bis(diphenylphosphino)ethane

DPPM

1,1-Bis(diphenylphosphino)methane

dr

Diastereoisomeric ratio

EDC

Ethyl-(N′,N′-dimethylamino)propylcarbodiimide hydrochloride

ee

Enantiomeric excess

er

Enantiomeric ratio

Fc

Ferrocenyl

Is

2,4,6-Tris(isopropyl)phenyl

L

Ligand

LDBB

Lithium P,P′-di-tert-butylbiphenylide

LPL

Lipoprotein lipase

Mes

Mesityl

Mnt

(1R,2S,5R)-Menthyl

Ms

Mesyl (Methanesulfol)

Nphth

Naphthyl

PFL

Pseudomonas fluorescens lipase

Piv

Pivaloyl

PLE

Pig (porcine) liver esterase

PPL

Porcine pancreatic lipase

РТЕ

Phosphotriesterase

PTSA

p-Toluenesulfonic acid

Py

Pyridine

RT

Room temperature

TBME

tert-Butylmethyl ether

TfO

Triflate

Tol

Tolyl

Ts

Tosyl

WSCI

Water soluble carbodiimide (EDC)

Xyl

Xylyl

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© Springer International Publishing Switzerland 2014

Authors and Affiliations

  1. 1.Institute of Bioorganic Chemistry and PetrochemistryNational Academy of Sciences of UkraineKievUkraine

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