CHELATION CONTROLLED ADDITION OF ETHYL PYRUVATE TO CYCLIC ALLYLIC STANNANES - A DIASTEREOSPECIFIC ROUTE TO FUNCTIONALIZED BICYCLIC GAMMA-LACTONES

Authors
MUDERAWAN IW BOTT RC YOUNG DJ
Citation
Iw. Muderawan et al., CHELATION CONTROLLED ADDITION OF ETHYL PYRUVATE TO CYCLIC ALLYLIC STANNANES - A DIASTEREOSPECIFIC ROUTE TO FUNCTIONALIZED BICYCLIC GAMMA-LACTONES, Synthesis, (11), 1998, pp. 1640-1644
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
11
Year of publication
1998
Pages
1640 - 1644
Database
ISI
SICI code
0039-7881(1998):11<1640:CCAOEP>2.0.ZU;2-7
Abstract
Methyltin trichloride and indium(III) chloride promote ethyl pyruvate addition to cyclic allylic stannanes to produce alpha-methyl-alpha-hyd roxy esters with excellent threo-diastereoselectivity (92-100% de). Th ese reactions probably proceed via an initial gamma-anti transmetallat ion followed by a metallo-ene cycloaddition involving internal chelati on. The resulting esters can be diastereospecifically converted to the corresponding bicyclic bromolactones.