Convenient method for synthesis of chiral C1-symmetric pyrrolidine derivative

被引:0
作者
Arif, Khaja Md. [1 ]
机构
[1] Govt Degree & PG Coll, Jammikunta 505122, Karimnagar, India
来源
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY | 2017年 / 56卷 / 08期
关键词
Asymmetric transformations; pyrrolidine derivatives; C-1-symmetric; diasteteomers separation; chiral allenes; ENANTIOSELECTIVE SYNTHESIS; YLIDE ROUTE; LIGANDS; ALLENES;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrrolidine derivatives are saturated N-heterocyclic compounds widely present in a large number of natural products, alkaloids and biologically active compounds. In this article, is reported the facile synthesis of chiral C-1-symmetric (S)-2-(anthracen-10-y1)-14(R)-1-phenylethy)pyrrolidine and (R)-2(anthracen-10-y1)-14(S)-1-phenylethyl)pyrrolidine diastereomers. These pyrrolidine derivatives are extremely useful for asymmetric transformations and enantioselective synthesis of chiral allenes.
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页码:897 / 899
页数:3
相关论文
共 14 条
[1]   Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].
Aggarwal, VK ;
Winn, CL .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620
[2]   Developments of asymmetric synthesis mediated by chiral sulfur reagents [J].
Blot, V ;
Brière, JF ;
Davoust, M ;
Minière, S ;
Reboul, V ;
Metzner, P .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (5-6) :1171-1182
[3]   C2-SYMMETRICAL BIS(PHOSPHOLANES) AND THEIR USE IN HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8518-8519
[4]   NEW ELECTRON-RICH CHIRAL PHOSPHINES FOR ASYMMETRIC CATALYSIS [J].
BURK, MJ ;
FEASTER, JE ;
HARLOW, RL .
ORGANOMETALLICS, 1990, 9 (10) :2653-2655
[5]   C1-symmetric monosubstituted chiral diene ligands in asymmetric rhodium-catalyzed 1,4-addition reactions [J].
Gendrineau, Thomas ;
Chuzel, Olivier ;
Eijsberg, Hendrik ;
Genet, Jean-Pierre ;
Darses, Sylvain .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (40) :7669-7672
[6]   Olefination of ketenes for the enantioselective synthesis of allenes via an ylide route [J].
Li, Chuan-Ying ;
Zhu, Ben-Hu ;
Ye, Long-Wu ;
Jing, Qing ;
Sun, Xiu-Li ;
Tang, Yong ;
Shen, Qi .
TETRAHEDRON, 2007, 63 (33) :8046-8053
[7]   Enantioselective synthesis of allenic esters via an ylide route [J].
Li, Chuan-Ying ;
Sun, Xiu-Li ;
Jing, Qing ;
Tang, Yong .
CHEMICAL COMMUNICATIONS, 2006, (28) :2980-2982
[8]   REDUCTIVE AMINATION OF 1,4-DICARBONYL AND 1,5-DICARBONYL COMPOUNDS WITH (S)-VALINE METHYL-ESTER - SYNTHESIS OF (S)-2-PHENYLPYRROLIDINE AND (S)-2-PHENYLPIPERIDINE [J].
MANESCALCHI, F ;
NARDI, AR ;
SAVOIA, D .
TETRAHEDRON LETTERS, 1994, 35 (17) :2775-2778
[9]   ORGANOBORON COMPOUNDS IN ORGANIC-SYNTHESIS .1. ASYMMETRIC HYDROBORATION [J].
MASAMUNE, S ;
KIM, BM ;
PETERSEN, JS ;
SATO, T ;
VEENSTRA, SJ ;
IMAI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (15) :4549-4551
[10]  
Periasamy M, 2009, SYNTHESIS-STUTTGART, V10, P1739