HYDROZIRCONATION OF ALLENYLSTANNANE FOR GENERATING BIMETALLIC 3-CARBON SPECIES - SYNTHESIS OF (E)-1,3-DIENES FROM CARBONYL-COMPOUNDS

Authors
MAETA H HASEGAWA T SUZUKI K
Citation
H. Maeta et al., HYDROZIRCONATION OF ALLENYLSTANNANE FOR GENERATING BIMETALLIC 3-CARBON SPECIES - SYNTHESIS OF (E)-1,3-DIENES FROM CARBONYL-COMPOUNDS, Synlett, (5), 1993, pp. 341-343
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1993
Pages
341 - 343
Database
ISI
SICI code
0936-5214(1993):5<341:HOAFGB>2.0.ZU;2-T
Abstract
Hydrozirconation of allenylstannane 4 generates (E) allylzirconocene s pecies 5 with a gamma-Bu3Sn substituent. This species reacts with alde hydes and ketones in highly regio- and stereoselective manner, and sub sequent in situ-treatment with BF3.OEt2 (Or CF3COOH) effects the beta- elimination to give terminal 1,3-dienes with high (E) selectivity. Mec hanistic rationale is proposed for the high geometrical selectivity.