Enantioselective synthesis of secondary phosphine oxides from (RP)-(-)-menthylhydrogenophenylphosphinate

被引：49
作者：
Leyris, Adeline [1 ]
Bigeault, Julie [1 ]
Nuel, Didier [1 ]
Giordano, Laurent [1 ]
Buono, Gerard [1 ]
机构：
[1] Univ Aix Marseille 3, Fac Sci St Jerome, CNRS, UMR 6180,Ecole Cent Marseille, F-13397 Marseille 20, France
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 30期
关键词：
chiral secondary phosphine oxides; (-)-menthol; enantioselective synthesis; diastereomerically pure phosphinate;
D O I：
10.1016/j.tetlet.2007.05.140
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Alkyl- and arylphenylphosphine oxides can easily be synthesized with an excellent enantiomeric excess starting from diastereomerically pure (Rp)-(-)-menthylhydrogenophenylphosphinate and organometallic reagents. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5247 / 5250
页数：4
相关论文
共 18 条
  • [1] [2+1] cycloadditions of terminal alkynes to norbornene derivatives catalyzed by palladium complexes with phosphinous acid ligands
    Bigeault, J
    Giordano, L
    Buono, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (30) : 4753 - 4757
  • [2] A superior method for the reduction of secondary phosphine oxides
    Busacca, CA
    Lorenz, JC
    Grinberg, N
    Haddad, N
    Hrapchak, M
    Latli, B
    Lee, H
    Sabila, P
    Saha, A
    Sarvestani, M
    Shen, S
    Varsolona, R
    Wei, XD
    Senanayake, CH
    [J]. ORGANIC LETTERS, 2005, 7 (19) : 4277 - 4280
  • [3] Air-stable P-stereogenic secondary phosphine oxides as chiral monodentate ligands for asymmetric catalytic carbon-carbon bond formation
    Dai, WM
    Yeung, KKY
    Leung, WH
    Haynes, RK
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (18) : 2821 - 2826
  • [4] New procedures for the resolution of chiral tert-butylphenylphosphine oxide and some of its reactions
    Drabowicz, J
    Lyzwa, P
    Omelanczuk, J
    Pietrusiewicz, KM
    Mikolajczyk, M
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (14) : 2757 - 2763
  • [5] UNSYMMETRICAL SECONDARY PHOSPHINE OXIDES . SYNTHETIC ISOTOPIC EXCHANGE AND STEREOCHEMICAL STUDIES
    EMMICK, TL
    LETSINGE.RL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (13) : 3459 - &
  • [6] STEREOSPECIFIC ALKYLATION OF MENTHYL PHENYLPHOSPHINATE
    FARNHAM, WB
    MURRAY, RK
    MISLOW, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (19) : 5809 - &
  • [7] SYNTHETIC UTILIZATION OF HIGHLY STEREOSELECTIVE CONJUGATE ADDITION-REACTIONS OF PHOSPHORUS AND SULFUR STABILIZED ALLYLIC CARBANIONS
    FREEMAN, R
    HAYNES, RK
    LOUGHLIN, WA
    MITCHELL, C
    STOKES, JV
    [J]. PURE AND APPLIED CHEMISTRY, 1993, 65 (04) : 647 - 654
  • [8] 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
    [J]. TETRAHEDRON LETTERS, 1996, 37 (27) : 4729 - 4732
  • [9] PREPARATION OF ENANTIOMERICALLY PURE TERTIARY PHOSPHINE OXIDES FROM, AND ASSAY OF ENANTIOMERIC PURITY WITH, (R(P))-TERT-BUTYLPHENYLPHOSPHINOTHIOIC AND (S-P)-TERT-BUTYLPHENYLPHOSPHINOTHIOIC ACIDS
    HAYNES, RK
    FREEMAN, RN
    MITCHELL, CR
    VONWILLER, SC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) : 2919 - 2921
  • [10] Haynes RK, 2000, EUR J ORG CHEM, V2000, P3205
12