(S,S)-4,4′-bis(3-hydroxy-estra-1,3,5(10),6,8-pentaene):: An efficient ligand for the catalytic asymmetric oxidation of sulfides to sulfoxides

被引：0
|
作者：
Bolm, C [1 ]
Dabard, OAG [1 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
来源：
SYNLETT | 1999年 / 03期
关键词：
sulfide oxidation; titanium; steroids; BINOL; asymmetric catalysis;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Optically active sulfoxides are obtained by titanium-catalyzed oxidation of prochiral sulfides using tert-butyl hydroperoxide (TBHP) as oxidant and steroid-derived BINOL derivative (S,S)-1 as chiral ligand. Good yields and enantioselectivities of up to 92% ee have been achieved.
引用
收藏
页码：360 / 362
页数：3
相关论文
共 50 条
  • [21] Regio- and stereoselective aspects in the oxidation of (R) and (S) 4a-methyl-(4,4a,5,6,7,8)-hexahydro-2(3H)naphthalenones in living rats
    Verite, P
    Menager, S
    Cave, C
    Andre, D
    dAngelo, J
    Revial, G
    Farnoux, CC
    Lafont, O
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (05) : 587 - 592
  • [22] Synthesis of(1R,2S,3S,4R,5R,7S)-2,3,4-tris(phenylmethoxy)-6,8-dioxabicyclo(3.2.1)octan-7-ol from 1R,2R,3S-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene by ozonolysis
    Mereyala, HB
    Chadalawada, B
    Guntha, S
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1999, 38 (02): : 207 - 209
  • [23] Crystal structure of 5,5′-((3-hydroxy-4-methoxyphenyl)methylene)bis(1,3-diethyl-6-hydroxy-2-thioxo-2,3-dihydropyrimidin-4(1H)-one), C24 H30N4O6S2
    Altowyan, Mezna Saleh
    Ali, M.
    AlRuqi, Obaid S.
    Al-Majid, Abdullah Mohammed
    Barakat, Assem
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2018, 233 (05): : 919 - 921
  • [24] Crystal structure of 4,4′-bipyridine 3-(sulfonyl-glycine)benzoic acid (1:1), C10H8N2 • C6H5O6S
    Guo, Hui
    Liu, Jing
    Lu, Xiao-Wei
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2007, 222 (04): : 437 - 438
  • [25] SYNTHESIS, CHARACTERIZATION, AND ELECTROCHEMISTRY OF A NEW PLATINUM TETRATHIOLENE CLUSTER, C10H4S4PT2(P(C6H5)3)4 - NOVEL SYSTEM WITH 5 REVERSIBLE OXIDATION-STATES
    TEO, BK
    WUDL, F
    MARSHALL, JH
    KRUGER, A
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (07) : 2349 - 2350
  • [26] Crystal structure of (P,1"S,2"R,5"S)-menthyl 4,4′-di-tert-butyl-2′-hydroxy-2,3,3′-trimethoxy-6′-methyl-1,1′-biphenyl-6-carboxylate, C6H(OCH3)2[C(CH3)3]CO2(C10H19)C6H(CH3)(OH)(OCH3)[C(CH3)3]
    Peters, K
    Peters, EM
    Pabst, T
    Bringmann, G
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2000, 215 (03): : 403 - 404
  • [27] Crystal structure of 25,27-bis(1,3,5-trimethyl-1,3,5-triaza-2λ5σ4-phosphorin-4,6-dionyl)calix[4]arene-crown-6-disulfide,C48H58N6O12P2S2
    Dieleman, CB
    Matt, D
    Neda, I
    Schmutzler, R
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2002, 217 (01): : 55 - 56
  • [28] First stereoselective total synthesis of 4(S),5(S)-oxido-17(S)-hydroxy-6(E),8(E),10(Z),13(Z),15(E),19(Z)-docosahexaenoic acid, the biosynthetic precursor of resolvins D3 and D4
    Nshimiyimana, Robert
    Lam, Ting Fung
    Aggarwal, Shubhangi
    Serhan, Charles N.
    Petasis, Nicos A.
    RSC ADVANCES, 2022, 12 (19) : 11613 - 11618
  • [29] Bis[(2R,6S)-4-(5-amino-3-carboxy-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2,6-dimethylpiperazin-1-ium] sulfate pentahydrate
    Li, Tao
    Yang, Lin
    Wang, Yuan Cheng
    Lian, Qiang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3366 - U905
  • [30] Practical asymmetric synthesis of (S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione, a key intermediate for the synthesis of irinotecan and other camptothecin analogs
    Henegar, KE
    Ashford, SW
    Baughman, TA
    Sih, JC
    Gu, RL
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19): : 6588 - 6597
12345