Stereospecific deoxygenation of phosphine oxides with retention of configuration using triphenylphosphine or triethyl phosphite as an oxygen acceptor

被引：95

作者：

Wu, HC ^{[1
]}

Yu, JQ ^{[1
]}

Spencer, JB ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 25期

关键词：

D O I：

10.1021/ol048227c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new protocol for deoxygenation of various phosphine oxides with retention of configuration is described. The advantage of the new method includes milder conditions and considerably shortened reaction times. Mechanistic studies about the oxygen transfer between the starting phosphine oxide and the sacrificial triphenylphosphine are also presented.

引用

收藏

页码：4675 / 4678

页数：4

相关论文

共 19 条

[1] SYNTHESIS OF CHIRAL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) VIA A NOVEL NICKEL-CATALYZED PHOSPHINE INSERTION [J].

CAI, DW ;

PAYACK, JF ;

BENDER, DR ;

HUGHES, DL ;

VERHOEVEN, TR ;

REIDER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7180-7181

[2] LIGAND ELECTRONIC EFFECTS IN ASYMMETRIC CATALYSIS - ENHANCED ENANTIOSELECTIVITY IN THE ASYMMETRIC HYDROCYANATION OF VINYLARENES [J].

CASALNUOVO, AL ;

RAJANBABU, TV ;

AYERS, TA ;

WARREN, TH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :9869-9882

[3] Synthesis and resolution of (R*,R*)-(±)-1,1,4,7,10,10-hexaphenyl-1,10-diarsa-4,7-diphosphadecane:: New ligand for the stereoselective self-assembly of dicopper(I), disilver(I), and digold(I) helicates [J].

Cook, VC ;

Willis, AC ;

Zank, J ;

Wild, SB .

INORGANIC CHEMISTRY, 2002, 41 (07) :1897-1906

[4] TITANIUM (IV) CATALYSIS IN THE REDUCTION OF PHOSPHINE OXIDES [J].

COUMBE, T ;

LAWRENCE, NJ ;

MUHAMMAD, F .

TETRAHEDRON LETTERS, 1994, 35 (04) :625-628

[5] New P-chirogenic phosphine ligands and their use in catalytic asymmetric reactions [J].

Crépy, KVL ;

Imamoto, T .

NEW ASPECTS IN PHOSPHORUS CHEMISTRY III, 2003, 229 :1-40

[6] RESOLUTION OF CPMO(NO)X(ETA-3-2-METHALLYL) COMPLEXES AND THEIR ENANTIOSELECTIVE REACTIONS WITH AN ALDEHYDE [J].

FALLER, JW ;

NGUYEN, JT ;

ELLIS, W ;

MAZZIERI, MR .

ORGANOMETALLICS, 1993, 12 (04) :1434-1438

[7] Asymmetric hydrosilylation of styrenes catalyzed by palladium-MOP complexes: Ligand modification and mechanistic studies [J].

Hayashi, T ;

Hirate, S ;

Kitayama, K ;

Tsuji, H ;

Torii, A ;

Uozumi, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1441-1449

[8]

Horner L., 1965, TETRAHEDRON LETT, V6, P1157

[9] Stereospecific reduction of phosphine oxides to phosphines by the use of a methylation reagent and lithium aluminum hydride [J].

Imamoto, T ;

Kikuchi, S ;

Miura, T ;

Wada, Y .

ORGANIC LETTERS, 2001, 3 (01) :87-90

[10]

LU XY, 1985, HUAXUE XUEBAO, P450