Highly Efficient, Enantioselective Syntheses of (S)-(+)- and (R)-(-)-Dapoxetine Starting with 3-Phenyl-1-propanol

被引：40
|
作者：
Kang, Soyeong
Lee, Hyeon-Kyu [1 ]
机构：
[1] Korea Res Inst Chem Technol, Drug Discovery Div, Taejon 305600, South Korea
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 01期
关键词：
X-RAY CRYSTALLOGRAPHY; DAPOXETINE HYDROCHLORIDE; FLUOXETINE; RESOLUTION; INHIBITOR; CHIRALITY;
D O I：
10.1021/jo902176s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient, enantioselective sequence has been developed for the synthesis of (S)- and (R)-dapoxetine. The pathways involve the intermediacy of the 6-membered-ring sulfamate esters 4, which were generated by Du Bois asymmetric C-H amination reactions of the prochiral sulfamate 3, catalyzed by the chiral dirhodium(II) complexes. During the Course of our research, the absolute configuration of the enantiomer of 4-pheny[1,2,3]oxathiazinane 2,2-dioxide (4r), prepared by the Du Bois asymmetric C-H amination reaction of 3 and the Rh-2(S-naP)(4) catalyst, is determined to be R and not S as wits originally reported.
引用
收藏
页码：237 / 240
页数：4
相关论文
共 50 条
  • [41] SYNTHESES OF ALPHA-PHENYLNEOPENTYL CHLORIDE ENANTIOMERS - (S)-(-)-1-CHLORO-1-PHENYL-2,2-DIMETHYLPROPANE FROM (R)-(+)-1-PHENYL-2,2-DIMETHYL-1-PROPANOL VIA THE REACTION OF TRI-N-BUTYLPHOSPHINE IN CARBON-TETRACHLORIDE AND (R)-(+)-1-CHLORO-1-PHENYL-2,2-DIMETHYLPROPANE FROM ANTHRANILIC ACID
    ZIEGER, HE
    BRIGHT, DA
    HAUBENSTOCK, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (08): : 1180 - 1184
  • [42] Short syntheses of (-)-(R)-pyrrolam A and (1S)-1-hydroxyindolizidin-3-one
    Schobert, Rainer
    Wicklein, Andre
    [J]. SYNTHESIS-STUTTGART, 2007, (10): : 1499 - 1502
  • [43] (3R,4S)-3-Phenyl-1-[(R)-1-phenyl-ethyl]-4-[(R)-1-phenylethylimino-methyl]azetidin-2-one
    [J]. Kooijman, Huub (h.kooijman@chem.uu.nl), 2000, International Union of Crystallography, 5 Abbey Road, Chester, CH1 2HU, United Kingdom (56)
  • [44] A convenient enantioselective synthesis of natural (1R,3S)-amidinomycin
    Nagata, H
    Taniguchi, T
    Ogasawara, K
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (16) : 2679 - 2681
  • [45] (1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol as an inhibitor of ceramidase
    Bielawska, A
    Greenberg, MS
    Perry, D
    Jayadev, S
    Shayman, JA
    McKay, C
    Hannun, YA
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (21) : 12646 - 12654
  • [46] Enantioselective synthesis of 1,2-acetonide of (2S,3R)-3-N-Boc-3-amino-4-phenyl-1,2-butanediol
    Remuzon, P
    Dussy, C
    Jacquet, JP
    Roty, P
    Bouzard, D
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (04) : 1181 - 1188
  • [47] Highly enantioselective catalytic domino reaction: Synthesis of (R)-2-phenyl-2H-thiochromene-3-carbaldehyde in supercritical carbon dioxide
    Li, Zhen
    Chen, Jian-Gang
    Song, Li-Ping
    Liu, Zhong-Wen
    Xue, Dong
    Liu, Zhao-Tie
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (12) : 1854 - 1856
  • [48] Highly enantioselective catalytic domino reaction: Synthesis of (R)-2-phenyl-2H-thiochromene-3-carbaldehyde in supercritical carbon dioxide
    Zhen Li
    Jian-Gang Chen
    Li-Ping Song
    Zhong-Wen Liu
    Dong Xue
    Zhao-Tie Liu
    [J]. Russian Journal of Organic Chemistry, 2013, 49 : 1854 - 1856
  • [49] FACILE AND EFFICIENT SYNTHESES OF NOVEL (S)-3-FLUOROPYRROLIDINE AND (R)-3-FLUOROPYRROLIDINE AND 3,3-DIFLUOROPYRROLIDINE
    GIARDINA, G
    DONDIO, G
    GRUGNI, M
    [J]. SYNLETT, 1995, (01) : 55 - 57
  • [50] Asymmetric syntheses of (1r,3R,4S)- and (1s,3R,4S)-(3,4-difluorocyclopentyl)-alanine derivatives
    Simpson, Robert D.
    Zhao, Wei
    [J]. TETRAHEDRON-ASYMMETRY, 2009, 20 (13) : 1515 - 1520
12345