PTC in OPRD: An illustrative overview

被引:25
作者
Ikunaka, Masaya [1 ]
机构
[1] Nagase & Co Ltd, Ctr Res & Dev, Nishi Ku, Kobe, Hyogo 6512241, Japan
关键词
D O I
10.1021/op700262h
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Illustrative examples of phase transfer catalysis (PTC) are compiled, albeit arbitrarily, to demonstrate its applicability to organic process research and development (OPRD), which covers eleven types of reactions: (1) ether formation, (2) ester formation, (3) hydrolytic removal of O-acetyl and O-silyl groups, (4) ester hydrolysis, (5) one-pot transesterification, (6) inorganic anionic species-mediated oxidation, (7) activation of KF for the fluoride-elicited nucleophilic displacement, (8) dichlorocarbene generation, (9) C-C bond formation in racemic synthesis, (10) asymmetric C-C bond formation in enantioselective synthesis of alpha-amino acids and alpha-hydroxy acids, and (11) enantio- and diasterocontrolled nitroaldol reactions.
引用
收藏
页码:698 / 709
页数:12
相关论文
共 66 条
[1]  
Abdel-Magid AF, 2004, ACS SYM SER, V870, P181
[2]   Hydrolysis of polypeptide esters with tetrabutylammonium hydroxide [J].
Abdel-Magid, AF ;
Cohen, JH ;
Maryanoff, CA ;
Shah, RD ;
Villani, FJ ;
Zhang, F .
TETRAHEDRON LETTERS, 1998, 39 (21) :3391-3394
[3]   2,2-DIETHOXY-1-ISOCYANOETHANE (2,2-Diethoxyethyl isocyanide, Isocyanoacetaldehyde diethyl acetal) [J].
Amato, Francesco ;
Marcaccini, Stefano .
ORGANIC SYNTHESES, 2005, 82 :18-+
[4]   Asymmetric phase-transfer catalyzed glycolate alkylation, investigation of the scope, and application to the synthesis of (-)-ragaglitazar [J].
Andrus, MB ;
Hicken, EJ ;
Stephens, JC ;
Bedke, DK .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9470-9479
[5]   Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation [J].
Andrus, Merritt B. ;
Hicken, Erik J. ;
Stephens, Jeffrey C. ;
Bedke, D. Karl .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) :8651-8654
[6]  
ANELLI PL, 1987, J ORG CHEM, V52, P2559
[7]  
Astleford B. A., 1997, CHIRALITY IND, P99
[8]   Practical synthesis of BILA 2157 BS, a potent and orally active renin inhibitor:: Use of an enzyme-catalyzed hydrolysis for the preparation of homochiral succinic acid derivatives [J].
Beaulieu, PL ;
Gillard, J ;
Bailey, M ;
Beaulieu, H ;
Duceppe, JS ;
Lavallée, P ;
Wernic, D .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6622-6634
[9]   SYNTHESIS AND ANTIVIRAL ACTIVITY OF THE NUCLEOTIDE ANALOG (S)-1-[3-HYDROXY-2-(PHOSPHONYLMETHOXY)PROPYL]CYTOSINE [J].
BRONSON, JJ ;
GHAZZOULI, I ;
HITCHCOCK, MJM ;
WEBB, RR ;
MARTIN, JC .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1457-1463
[10]   Chiral 1,3-cyclobutane amino acids: Syntheses and extended conformations [J].
Burgess, K ;
Li, SM ;
Rebenspies, J .
TETRAHEDRON LETTERS, 1997, 38 (10) :1681-1684