DERACEMIZATION OF A PHOSPHINE OXIDE VIA ENANTIOSELECTIVE PROTONATION

被引:26
|
作者
VEDEJS, E
GARCIARIVAS, JA
机构
[1] Chemistry Department, University of Wisconsin, Madison
来源
JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 22期
关键词
D O I
10.1021/jo00101a008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of the phosphine oxide anion 2 with the keto aniline 3c affords (S)-1 with 81-83% ee, and one crystallization upgrades the material to (S)-1 with > 99% ee (78% overall yield).
引用
收藏
页码:6517 / 6518
页数:2
相关论文
共 50 条
  • [31] ENANTIOSELECTIVE DEHYDROHALOGENATION VIA ASYMMETRIC DEPROTONATION BY CHIRAL LITHIUM AMIDES - DERACEMIZATION OF A COMPOUND BEARING A CHIRAL AXIS
    DUHAMEL, L
    RAVARD, A
    PLAQUEVENT, JC
    DAVOUST, D
    TETRAHEDRON LETTERS, 1987, 28 (45) : 5517 - 5520
  • [32] Catalytic enantioselective decarboxylative protonation
    Mohr, Justin T.
    Nishimata, Toyoki
    Behenna, Douglas C.
    Stoltz, Brian M.
    Journal of the American Chemical Society, 2006, 128 (35): : 11348 - 11349
  • [33] Catalytic enantioselective decarboxylative protonation
    Mohr, Justin T.
    Nishimata, Toyoki
    Behenna, Douglas C.
    Stoltz, Brian M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (35) : 11348 - 11349
  • [34] PHOSPHINE BASICITIES AS DETERMINED BY ENTHALPIES OF PROTONATION
    BUSH, RC
    ANGELICI, RJ
    INORGANIC CHEMISTRY, 1988, 27 (04) : 681 - 686
  • [35] Enantioselective cyanosilylation of aldehydes catalyzed by Mn(salen) complex/triphenyl phosphine oxide
    Kim, Sung Soo
    Kwak, Ju Myung
    George, Soney C.
    APPLIED ORGANOMETALLIC CHEMISTRY, 2007, 21 (09) : 809 - 813
  • [36] Enantioselective Morita-Baylis-Hillman reaction catalyzed by a chiral phosphine oxide
    Kotani, Shunsuke
    Ito, Masaya
    Nozaki, Hirono
    Sugiura, Masaharu
    Ogasawara, Masamichi
    Nakajima, Makoto
    TETRAHEDRON LETTERS, 2013, 54 (48) : 6430 - 6433
  • [37] Enantioselective direct aldol reactions promoted by phosphine oxide aziridinyl phosphonate organocatalysts
    Dogan, Ozdemir
    Tan, Duygu
    TETRAHEDRON-ASYMMETRY, 2015, 26 (23) : 1348 - 1353
  • [38] Deracemization of aryl secondary alcohols via enantioselective oxidation and stereoselective reduction with tandem whole-cell biocatalysts
    Li, Yun-Long
    Xu, Jian-He
    Xu, Yi
    JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2010, 64 (1-2) : 48 - 52
  • [39] Progress in Enantioselective Phosphine Organocatalysis
    Tang, Qian
    Tu, Aiping
    Deng, Zhenzhen
    Hu, Mengying
    Zhong, Weihui
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (05) : 954 - 970
  • [40] Synthesis of Unsymmetrical Bis(phosphine) Oxides and Their Phosphines via Secondary Phosphine Oxide Precursors
    Pedroarena, James R.
    Nell, Bryan P.
    Zakharov, Lev N.
    Tyler, David R.
    JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS, 2020, 30 (01) : 196 - 205