ASYMMETRIC MICHAEL ADDITION OF THIOLS TO (1R,2R,4R)-(-)2,10-N-ENOYLCAMPHORSULTAM

被引：19
作者：
TSAI, WJ
LIN, YT
UANG, BJ
机构：
[1] NATL TSING HUA UNIV,DEPT CHEM,HSINCHU 30043,TAIWAN
[2] CHINA STEEL CORP,DEPT NEW MAT RES & DEV,KAOHSIUNG 81233,TAIWAN
来源：
TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 07期
关键词：
D O I：
10.1016/0957-4166(94)80155-X
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Lithium base promoted stereoselective Michael addition of thiols to N-methacryloylcamphorsultam produced the corresponding addition products in 66% to 90% diastereoselectivity. Hydrolysis of the Michael product with three equivalents of lithium hydroxide in THF/H2O gave the corresponding optically active beta-thioester with no sign of any racemization, and recovered camphorsultam quantitatively.
引用
收藏
页码：1195 / 1198
页数：4
相关论文
共 50 条
  • [41] Bioconversion of indene to cis (1S,2R) indandiol and trans (1R,2R) indandiol by Rhodococcus species
    Chartrain, M
    Jackey, B
    Taylor, C
    Sandford, V
    Gbewonyo, K
    Lister, L
    Dimichele, L
    Hirsch, C
    Heimbuch, B
    Maxwell, C
    Pascoe, D
    Buckland, B
    Greasham, R
    JOURNAL OF FERMENTATION AND BIOENGINEERING, 1998, 86 (06): : 550 - 558
  • [42] Enzymatic (2R,4R)-Pentanediol Synthesis - "Putting a Bottle on the Table"
    Sehl, Torsten
    Seibt, Lisa
    Kappauf, Katrin
    Ergezinger, Pia
    Spoering, Jan-Dirk
    Mielke, Kristina
    Doeker, Moritz
    Verma, Neha
    Bocola, Marco
    Daussmann, Thomas
    Chen, Haibin
    Shi, Shumin
    Jupke, Andreas
    Rother, Doerte
    CHEMIE INGENIEUR TECHNIK, 2023, 95 (04) : 557 - 564
  • [43] CRYSTAL-STRUCTURE AND CIRCULAR-DICHROISM OF (1R,3R,4R), (1R,3R,4R)-(BORNANE 2-ONE,3-YL)-3 BORNANE 2-ONE (DICAMPHOR)
    LAMAZOUERE, AM
    ELBATOUTI, N
    SOTIROPOULOS, J
    DUPONT, L
    GERMAIN, G
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE, 1994, 209 (03): : 263 - 266
  • [44] STRUCTURE AND ABSOLUTE-CONFIGURATION OF (1R,2R,4R)-2-[2-(4-BROMOBENZOYLOXY)ETHYL]-1-METHYLBICYCLO[2.1.1]HEXAN-5-ONE
    RETTIG, SJ
    TROTTER, J
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1987, 43 : 691 - 693
  • [45] tert-Butyl N-[(1R,2R)-2-(isothiocyanato)-cyclohexyl]carbamate
    Zhong, Ming
    Siegler, Maxime
    Long, Sihui
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O3589 - U4253
  • [46] Synthesis of (1R,2R)- and (1S,2R)-1,2-Epoxy-3-hydroxypropylphosphonates as Analogues of Fosfomycin
    Wroblewski, Andrzej E.
    Szewczyk, Eligia M.
    Bak-Sypien, Irena I.
    ARCHIV DER PHARMAZIE, 2009, 342 (09) : 521 - 527
  • [47] Asymmetric synthesis of (2R,4R,5S)tetrahydropseudodistomin and stereoisomers by cycloaddition of nitrone to vinylglycinol
    Kiguchi, T.
    Ikai, M.
    Shirakawa, M.
    Fujimoto, K.
    Jornal of the Chemical Society. Perkin Transactions 1, (05):
  • [48] Asymmetric synthesis of (2R,4R,5S)-tetrahydropseudodistomin and stereoisomers by cycloaddition of nitrone to vinylglycinol
    Kiguchi, T
    Ikai, M
    Shirakawa, M
    Fujimoto, K
    Ninomiya, I
    Naito, T
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (05): : 893 - 899
  • [49] MEIOTIC BEHAVIOR OF CHROMOSOMES 1R, 2R AND 5R IN AUTOTETRAPLOID RYE
    NARANJO, T
    ORELLANA, J
    CHROMOSOMA, 1984, 89 (02) : 143 - 150
  • [50] (2R,4R)-1-(tert-Butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylic acid
    Yuan, Jing
    Cai, Zhi-Qiang
    Huang, Chang-Jiang
    Xu, Wei-Ren
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O3258 - U1428
12345