ASYMMETRIC DIELS-ALDER REACTIONS OF 2-FLUOROACRYLIC ACID-DERIVATIVES - PART 1 - THE CONSTRUCTION OF FLUORINE-SUBSTITUTED CHIRAL TERTIARY CARBON

Authors
ITO H SAITO A TAGUCHI T
Citation
H. Ito et al., ASYMMETRIC DIELS-ALDER REACTIONS OF 2-FLUOROACRYLIC ACID-DERIVATIVES - PART 1 - THE CONSTRUCTION OF FLUORINE-SUBSTITUTED CHIRAL TERTIARY CARBON, Tetrahedron : asymmetry, 9(11), 1998, pp. 1979-1987
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
11
Year of publication
1998
Pages
1979 - 1987
Database
ISI
SICI code
0957-4166(1998)9:11<1979:ADRO2A>2.0.ZU;2-H
Abstract
For the construction of chiral monofluorinated tertiary carbons, we ha ve examined the asymmetric Diels-Alder reaction of 2-fluoroacrylic aci d derivatives bearing a chiral oxazolidinone moiety. Under diethylalum inum chloride catalyzed conditions at -100 degrees C, the reaction of 1 with isoprene proceeded smoothly with high diastereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.