Highly diastereoselective reaction of 2-azanorbornyl enolates with electrophiles

被引：5

作者：

Alonso, DA ^{[1
]}

Nordin, SJM ^{[1
]}

Andersson, PG ^{[1
]}

机构：

[1] Univ Uppsala, Dept Organ Chem, S-75121 Uppsala, Sweden

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 10期

关键词：

D O I：

10.1021/ol990942c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly diastereoselective reaction of 2-azanorbornyl enolates with electrophiles has been studied. Deprotonation of 4 with LDA at low temperature affords the corresponding exocyclic lithium enolate 5, which reacts with different electrophiles such as alkyl halides, aldehydes and acyl chlorides to give the corresponding exo addition products 6, The products are formed in good yields and with diastereoselectivities above 95%.

引用

页码：1595 / 1597

页数：3

共 25 条

[1] DIASTEREOSELECTIVE AZA-DIELS-ALDER REACTION - USE OF 1-PHENYLETHYLIMINE OF ALKYL GLYOXYLATE FOR SYNTHESIS OF CYCLIC ALPHA-AMINO-ACIDS
ABRAHAM, H
STELLA, L
[J]. TETRAHEDRON, 1992, 48 (44) : 9707 - 9718
[2] (1S,3R,4R)-2-azanorbornylmethanol, an efficient ligand for ruthenium-catalyzed asymmetric transfer hydrogenation of ketones
Alonso, DA
Guijarro, D
Pinho, P
Temme, O
Andersson, PG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) : 2749 - 2751
[3] New expedient route to both enantiomers of nonproteinogenic α-amino acid derivatives from the unsaturated 2-aza-bicyclo moiety
Alonso, DA
Bertilsson, SK
Johnsson, SY
Nordin, SJM
Södergren, MJ
Andersson, PG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) : 2276 - 2280
[4] ALONSO DA, 1999, IN PRESS J AM CHEM S
[5] Torsional and steric effects control the stereoselectivities of alkylations of pyrrolidinone enolates
Ando, K
Green, NS
Li, Y
Houk, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (22) : 5334 - 5335
[6] Asymmetric synthesis of the core cyclopentane of viridenomycin
Arrington, MP
Meyers, AI
[J]. CHEMICAL COMMUNICATIONS, 1999, (15) : 1371 - 1372
[7] PALLADIUM-CATALYZED REDUCTION OF AN ALLYLIC AMINE - A FORMAL ACCESS TO BOTH DIASTEREOISOMERS OF CYCLOPENTENYL GLYCINE
BOURGEOISCURY, A
DOAN, D
GORE, J
[J]. TETRAHEDRON LETTERS, 1992, 33 (10) : 1277 - 1280
[8] Brandt P, 1999, CHEM-EUR J, V5, P1692, DOI 10.1002/(SICI)1521-3765(19990604)5:6<1692::AID-CHEM1692>3.0.CO
[9] 2-M
[10] CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO ALDEHYDES
COREY, EJ
HANNON, FJ
[J]. TETRAHEDRON LETTERS, 1987, 28 (44) : 5233 - 5236

← 1 2 3 →