Lipase-catalyzed resolution of 2-azabicyclo[2.2.1]hept-5-en-3-ones

被引：21

作者：

Nakano, H ^{[1
]}

Iwasa, K ^{[1
]}

Okuyama, Y ^{[1
]}

Hongo, H ^{[1
]}

机构：

[1] TOHOKU COLL PHARMACEUT SCI,AOBA KU,SENDAI,MIYAGI 981,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 08期

关键词：

D O I：

10.1016/0957-4166(96)00293-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The lipase-catalyzed asymmetric resolution of 2-azabicyclo[2.2.1] hept-5-en-3-ones is reported; non-racemic chiral 2-azabicyclo[2.2.1]hept-5-en-3-ones were obtained conveniently by lipase-catalyzed enantioselective transesterification or hydrolysis of N-hydroxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one or N-acyloxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one.

引用

页码：2381 / 2386

页数：6

共 50 条

[41] 2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics
Singh, Rohit
Vince, Robert
CHEMICAL REVIEWS, 2012, 112 (08) : 4642 - 4686
[42] SYNTHESIS OF EITHER ENANTIOMER OF CIS-3-AMINOCYCLOPENTANECARBOXYLIC ACID FROM BOTH ENANTIOMERS OF RACEMIC 2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONE
EVANS, C
MCCAGUE, R
ROBERTS, SM
SUTHERLAND, AG
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (03): : 656 - 657
[43] A ring-opening cross-metathesis reaction of N-trialkylsilyl 2-azabicyclo[2.2.1]hept-5-en-3-one with allyltrimethylsilane
Ishikura, M
Hasunuma, M
Yanada, K
HETEROCYCLES, 2005, 65 (11) : 2587 - 2592
[44] Inversion of enantioselectivity in the Diels-Alder synthesis of 2-azabicyclo[2.2.1]hept-5-en-3-one from cyclopentadiene and chiral sulfonyl cyanides
Blanco, JM
Caamano, O
Fernandez, F
GarciaMera, X
Nieto, I
RodriguezBorges, JE
HETEROCYCLES, 1997, 45 (09) : 1745 - 1750
[45] Regiochemistry of the reductive Heck coupling of 2-azabicyclo[2.2.1]hept-5-ene. Synthesis of epibatidine analogues
Kasyan, A
Wagner, C
Maier, ME
TETRAHEDRON, 1998, 54 (28) : 8047 - 8054
[46] Synthesis of epibatidine isomers: Reductive heck coupling of 2-azabicyclo[2.2.1]hept-5-ene derivatives
Cox, CD
Malpass, JR
TETRAHEDRON, 1999, 55 (40) : 11879 - 11888
[47] Oxymercuration of 2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-one: explanation of stereoselectivity
Palmer, CF
McCague, R
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (18): : 2977 - 2978
[48] SYNTHESIS OF NUCLEOSIDES AND RELATED-COMPOUNDS .20. SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES FROM 2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONES - SODIUM BOROHYDRIDE-MEDIATED CARBON NITROGEN BOND-CLEAVAGE OF 5-MEMBERED AND 6-MEMBERED LACTAMS
KATAGIRI, N
MUTO, M
NOMURA, M
HIGASHIKAWA, T
KANEKO, C
CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (05) : 1112 - 1122
[49] A NOVEL SKELETAL REARRANGEMENT OF 2-AZABICYCLO[2.2.1]HEPT-5-ENE-3-CARBOXYLIC ACID-DERIVATIVES INTO 2-OXABICYCLO[3.3.0]OCT-7-EN-3-ONES UNDER ACIDIC CONDITIONS
KOBAYASHI, T
ONO, K
KATO, H
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (01) : 61 - 65
[50] 2-Azabicyclo[2.2.1]hept-5-enes from 7-azabicyclo[2.2.1]heptadienes by tandem intermolecular radical addition-homoallylic radical rearrangement
Hodgson, DM
Bebbington, MWP
Willis, P
CHEMICAL COMMUNICATIONS, 2001, (10) : 889 - 890

← 1 2 3 4 5 →