共 22 条
Contrast performance in catalytic ability -: new cinchona phase transfer catalysts for asymmetric synthesis of α-amino acids
被引:14
作者:

Elango, S
论文数: 0 引用数: 0
h-index: 0
机构:
Inst Chem & Engn Sci, Jurong Isl 627833, Singapore Inst Chem & Engn Sci, Jurong Isl 627833, Singapore

Venugopal, M
论文数: 0 引用数: 0
h-index: 0
机构:
Inst Chem & Engn Sci, Jurong Isl 627833, Singapore Inst Chem & Engn Sci, Jurong Isl 627833, Singapore

Suresh, PS
论文数: 0 引用数: 0
h-index: 0
机构:
Inst Chem & Engn Sci, Jurong Isl 627833, Singapore Inst Chem & Engn Sci, Jurong Isl 627833, Singapore

Eni
论文数: 0 引用数: 0
h-index: 0
机构:
Inst Chem & Engn Sci, Jurong Isl 627833, Singapore Inst Chem & Engn Sci, Jurong Isl 627833, Singapore
机构:
[1] Inst Chem & Engn Sci, Jurong Isl 627833, Singapore
来源:
关键词:
chiral phase transfer catalyst;
cinchona alkaloids;
D O I:
10.1016/j.tet.2004.12.005
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
Two new cinchona phase transfer catalysts are prepared front dihydrocinchonidine using 13-picenytmethyl bromide and I-pyrenylmethyl bromide, respectively. A total contrast in catalytic efficiency is observed during the asymmetric alkylation of glycinate esters; with one catalyst, the reaction is either incomplete or the enantioselectivity is very poor (15% ee) while the other catalyst afforded high selectivity up to 94% ee. (C) 2004 Elsevier Ltd. All fights reserved.
引用
收藏
页码:1443 / 1447
页数:5
相关论文
共 22 条
- [1] Asymmetric PTC C-alkylation catalyzed by chiral derivatives of tartaric acid and aminophenols.: Synthesis of (R)- and (S)-α-methyl amino acids[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) : 7041 - 7048Belokon, YN论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaKochetkov, KA论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaChurkina, TD论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaIkonnikov, NS论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaChesnokov, AA论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaLarionov, OV论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaSingh, I论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaParmar, VS论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaVyskocil, S论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaKagan, HB论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia
- [2] Asymmetric PTC C-alkylation mediated by TADDOL -: novel route to enantiomerically enriched α-alkyl-α-amino acids[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (05) : 851 - 857Belokon, YN论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaKochetkov, KA论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaChurkina, TD论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaIkonnikov, NS论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaChesnokov, AA论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaLarionov, OV论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaParmár, VS论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaKumar, R论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaKagan, HB论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia
- [3] Chiral salen-metal complexes as novel catalysts for asymmetric phase transfer alkylations[J]. TETRAHEDRON LETTERS, 1999, 40 (33) : 6105 - 6108Belokon, YN论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaNorth, M论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaKublitski, VS论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaIkonnikov, NS论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaKrasik, PE论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, RussiaMaleev, VI论文数: 0 引用数: 0 h-index: 0机构: Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia
- [4] A practical asymmetric synthesis of α-methyl α-amino acids using a chiral Cu-salen complex as a phase transfer catalyst[J]. TETRAHEDRON LETTERS, 2000, 41 (37) : 7245 - 7248Belokon', YN论文数: 0 引用数: 0 h-index: 0机构: Kings Coll London, Dept Chem, London WC2R 2LS, EnglandDavies, RG论文数: 0 引用数: 0 h-index: 0机构: Kings Coll London, Dept Chem, London WC2R 2LS, EnglandNorth, M论文数: 0 引用数: 0 h-index: 0机构: Kings Coll London, Dept Chem, London WC2R 2LS, England Kings Coll London, Dept Chem, London WC2R 2LS, England
- [5] New dimeric anthracenyl-derived Cinchona quaternary ammonium salts as phase-transfer catalysts for the asymmetric synthesis of α-amino acids[J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (09) : 927 - 931Chinchilla, R论文数: 0 引用数: 0 h-index: 0机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, SpainMazón, P论文数: 0 引用数: 0 h-index: 0机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, SpainNájera, C论文数: 0 引用数: 0 h-index: 0机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain
- [6] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12414 - 12415Corey, EJ论文数: 0 引用数: 0 h-index: 0机构: Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USAXu, F论文数: 0 引用数: 0 h-index: 0机构: Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USANoe, MC论文数: 0 引用数: 0 h-index: 0机构: Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
- [7] An unusual electronic effect of an aromatic-F in phase-transfer catalysts derived from Cinchona-alkaloid[J]. ORGANIC LETTERS, 2002, 4 (24) : 4245 - 4248Jew, SS论文数: 0 引用数: 0 h-index: 0机构: Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea Seoul Natl Univ, Coll Pharm, Seoul 151742, South KoreaYoo, MS论文数: 0 引用数: 0 h-index: 0机构: Seoul Natl Univ, Coll Pharm, Seoul 151742, South KoreaJeong, BS论文数: 0 引用数: 0 h-index: 0机构: Seoul Natl Univ, Coll Pharm, Seoul 151742, South KoreaPark, IY论文数: 0 引用数: 0 h-index: 0机构: Seoul Natl Univ, Coll Pharm, Seoul 151742, South KoreaPark, HG论文数: 0 引用数: 0 h-index: 0机构: Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea
- [8] Synthesis and application of dimeric Cinchona alkaloid phase-transfer catalysts:: α,α′-bis[O(9)-allylcinchonidinium]-o, m, or p-xylene dibromide[J]. CHEMICAL COMMUNICATIONS, 2001, (14) : 1244 - 1245Jew, SS论文数: 0 引用数: 0 h-index: 0机构: Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea Seoul Natl Univ, Coll Pharm, Seoul 151742, South KoreaJeong, BS论文数: 0 引用数: 0 h-index: 0机构: Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea Seoul Natl Univ, Coll Pharm, Seoul 151742, South KoreaYoo, MS论文数: 0 引用数: 0 h-index: 0机构: Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea Seoul Natl Univ, Coll Pharm, Seoul 151742, South KoreaHuh, H论文数: 0 引用数: 0 h-index: 0机构: Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea Seoul Natl Univ, Coll Pharm, Seoul 151742, South KoreaPark, HG论文数: 0 引用数: 0 h-index: 0机构: Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea
- [9] IMPROVED PHENANTHRENE SYNTHESIS - SIMPLE ROUTE TO (+/-)-TYLOPHORINE[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (22) : 826 - 827LIEPA, AJ论文数: 0 引用数: 0 h-index: 0机构: AUSTRALIAN NATL UNIV,RES SCH CHEM,CANBERRA 2600,ACT,AUSTRALIA AUSTRALIAN NATL UNIV,RES SCH CHEM,CANBERRA 2600,ACT,AUSTRALIASUMMONS, RE论文数: 0 引用数: 0 h-index: 0机构: AUSTRALIAN NATL UNIV,RES SCH CHEM,CANBERRA 2600,ACT,AUSTRALIA AUSTRALIAN NATL UNIV,RES SCH CHEM,CANBERRA 2600,ACT,AUSTRALIA
- [10] Enantioselective synthesis of α-carbon deuterium-labelled L-α-amino acids[J]. TETRAHEDRON LETTERS, 2002, 43 (37) : 6677 - 6679Lygo, B论文数: 0 引用数: 0 h-index: 0机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandHumphreys, LD论文数: 0 引用数: 0 h-index: 0机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England