Enantioselective synthesis of alpha-hydroxy phosphonates using the LaLi(3)tris(binaphthoxide) catalyst (LLB), prepared by an improved method

被引：116

作者：

Sasai, H ^{[1
]}

Bougauchi, M ^{[1
]}

Arai, T ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 15期

关键词：

D O I：

10.1016/S0040-4039(97)00437-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

LaLi(3)tris(binaphthoxide) catalyst (LLB), which is prepared from LaCl3 . 7H(2)O(1 mol equiv), (R)- or (S)-BINOL dilithium salt (2.7 mol equiv), and NaO-t-Bu (0.3 mol equiv), is effective for the hydrophosphonylation of various aldehydes to give desired alpha-hydroxyphosphonates in up to 95% ee (88% yield). It is also noteworthy that with slow addition of the aldehydes the enantiomeric excesses of the products were increased. (C) 1997 Elsevier Science Ltd.

引用

页码：2717 / 2720

页数：4

共 42 条

[1] PHOSPHONOPEPTIDES AS ANTIBACTERIAL AGENTS - ALAPHOSPHIN AND RELATED PHOSPHONOPEPTIDES [J].

ALLEN, JG ;

ATHERTON, FR ;

HALL, MJ ;

HASSALL, CH ;

HOLMES, SW ;

LAMBERT, RW ;

NISBET, LJ ;

RINGROSE, PS .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 15 (05) :684-695

[2] Self-assembly of heterobimetallic complexes and reactive nucleophiles: A general strategy for the activation of asymmetric reactions promoted by heterobimetallic catalysts [J].

Arai, T ;

Yamada, YMA ;

Yamamoto, N ;

Sasai, H ;

Shibasaki, M .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (11) :1368-1372

[3] A new multifunctional heterobimetallic asymmetric catalyst for Michael additions and tandem Michael-Aldol reactions [J].

Arai, T ;

Sasai, H ;

Aoe, K ;

Okamura, K ;

Date, T ;

Shibasaki, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :104-106

[4] Catalytic asymmetric synthesis of alpha-hydroxy phosphonates using the Al-Li-BINOL complex [J].

Arai, T ;

Bougauchi, M ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :2926-2927

[5] PHOSPHONOPEPTIDES AS ANTIBACTERIAL AGENTS - MECHANISM OF ACTION OF ALAPHOSPHIN [J].

ATHERTON, FR ;

HALL, MJ ;

HASSALL, CH ;

LAMBERT, RW ;

LLOYD, WJ ;

RINGROSE, PS .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 15 (05) :696-705

[6]

BARALDI PG, 1982, SYNTHESIS-STUTTGART, P653

[7] REACTIONS OF CHIRAL PHOSPHORUS-ACID DIAMIDES - THE ASYMMETRIC-SYNTHESIS OF CHIRAL ALPHA-HYDROXY PHOSPHONAMIDES, PHOSPHONATES, AND PHOSPHONIC-ACIDS [J].

BLAZIS, VJ ;

KOELLER, KJ ;

SPILLING, CD .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :931-940

[8] Combinatorial method for the synthesis of alpha-hydroxy phosphonates on Wang resin [J].

Cao, XD ;

Mjalli, AMM .

TETRAHEDRON LETTERS, 1996, 37 (34) :6073-6076

[9] ENANTIOSELECTIVE SYNTHESIS OF DIETHYL 1-HYDROXYALKYLPHOSPHONATES VIA OXAZABOROLIDINE CATALYZED BORANE REDUCTION OF DIETHYL ALPHA-KETOPHOSPHONATES [J].

GAJDA, T .

TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1965-1972

[10] STUDIES ON THE BASE-PROMOTED ENANTIOSELECTIVE ALDOL REACTION BETWEEN AN (S,S)-2-OXO-2-PROPIONYL-1,3,2-OXAZAPHOSPHORINANE AND BENZALDEHYDE [J].

GORDON, NJ ;

EVANS, SA .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 75 (1-4) :47-50

← 1 2 3 4 5 →