STEREOCONTROL IN [4-ETHYL LACTATE WITH 2-SILOXY-1,3-BUTADIENES(2]TYPECYCLOADDITION OF AN ALDIMINE DERIVED FROM (S))

Authors
ISIMARU K WATANABE K YAMAMOTO Y AKIBA KY
Citation
K. Isimaru et al., STEREOCONTROL IN [4-ETHYL LACTATE WITH 2-SILOXY-1,3-BUTADIENES(2]TYPECYCLOADDITION OF AN ALDIMINE DERIVED FROM (S)), Synlett, (7), 1994, pp. 495-498
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
7
Year of publication
1994
Pages
495 - 498
Database
ISI
SICI code
0936-5214(1994):7<495:SI[LW2>2.0.ZU;2-E
Abstract
[4+2]Type cycloaddition of a chiral aldimine (1) derived from (S)-ethy l lactate with 2-siloxy-1,3-butadiene 2a was performed to give 4-piper idones 3a and 3b in high yields after treatment with TBAF. Relative st ereochemistry at 2- and 6-positions was trans for both isomers. Chelat ion-controlled product 3b was obtained selectively by use of TiCl4-i-P rCN at -30-degrees-C and 3a was provided using TMSOTf or Zn(OTf)2 at 4 -degrees-C with high selectivity.