A convenient multigram synthesis of highly enantioenriched methyl 3-silylglycidates

被引：18
|
作者：
Lowe, JT
Youngsaye, W
Panek, JS
机构：
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Ctr Chem Methodol & Lib Dev, Metcalf Ctr Sci & Engn, Boston, MA 02215 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 09期
关键词：
D O I：
10.1021/jo060134g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A multigram scale synthesis of the four stereoisomers of methyl 3-silylglycidates (epoxysilanes) with high enantiopurity is described. Key reactions include a Sharpless asymmetric epoxidation (SAE) of a trans-vinylsilane and an enzymatic resolution of a racemic cis-epoxysilane to establish the desired configurations. Few chromatographic separations (5 columns out of 13 steps) are required for purification, establishing a convenient reaction sequence for both the trans- and cis-isomers.
引用
收藏
页码：3639 / 3642
页数：4
相关论文
共 50 条
  • [1] Convenient multigram synthesis of (R)-homopipecolic acid methyl ester
    Breuning, M
    Steiner, M
    SYNTHESIS-STUTTGART, 2006, (08): : 1386 - 1389
  • [2] A VERSATILE AND CONVENIENT MULTIGRAM SYNTHESIS OF METHYLIDENEMALONIC ACID DIESTERS
    DEKEYSER, JL
    DECOCK, CJC
    POUPAERT, JH
    DUMONT, P
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20): : 4859 - 4862
  • [3] A convenient multigram scale synthesis of tetrahydrothiophene-3-one-1,1-dioxide
    Altenbach, RJ
    Kalvoda, L
    Carroll, WA
    SYNTHETIC COMMUNICATIONS, 2004, 34 (04) : 567 - 570
  • [4] An efficient multigram synthesis of juglone methyl ether
    Cui, Jia-hua
    Cui, Qing
    Zhang, Qi-jing
    Li, Shao-shun
    JOURNAL OF CHEMICAL RESEARCH, 2015, (09) : 553 - 554
  • [5] Convenient synthesis of pure fluorous alkyl azides at multigram scale
    Berta, Mate
    Dancso, Andras
    Nemes, Aniko
    Patho, Zoltan
    Szabo, Denes
    Rabai, Jozsef
    JOURNAL OF FLUORINE CHEMISTRY, 2017, 196 : 57 - 62
  • [6] Synthesis of enantioenriched methyl vic-dihydroxystearates
    Plate, M
    Overs, M
    Schäfer, HJ
    SYNTHESIS-STUTTGART, 1998, (09): : 1255 - 1258
  • [7] Toward the synthesis of enantioenriched and highly substituted δ-lactones
    Blakemore, James D.
    Guo, Fenghai
    Huang, Yaxin
    Dieter, R. Karl
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 68 - 68
  • [8] Convenient Multigram Synthesis of 4-Chloropyridine-2,6-dicarbonyl Dichloride
    Mitsui, Kazuhiko
    Parquette, Jon R.
    SYNTHESIS-STUTTGART, 2009, (05): : 713 - 714
  • [9] A Convenient Synthesis of (-)-Methyl Epijasmonate
    U, J. S.
    Park, H. S.
    Gupta, S.
    Cha, J. K.
    Synthetic Communications, 27 (17):
  • [10] A convenient synthesis of (-)-methyl epijasmonate
    Sun, J
    Park, HS
    Gupta, S
    Cha, JK
    SYNTHETIC COMMUNICATIONS, 1997, 27 (17) : 2931 - 2941
12345