ChemInform Abstract: Remote Stereocontrol in Carbonyl Additions Promoted by Vinylstannanes.

  1. Barbero, Asuncion 1
  2. Pulido, Francisco J. 1
  3. Rincon, Juan A. 1
  4. Cuadrado, Purificacion 1
  5. Galisteo, Diego 1
  6. Martinez-Garcia, Henar 1
  1. 1 Universidad de Valladolid
    info

    Universidad de Valladolid

    Valladolid, España

    ROR https://ror.org/01fvbaw18

Journal:
ChemInform

ISSN: 0931-7597,  1522-2667

Year of publication: 2010

Volume: 32

Issue: 38

Pages: no-no

Type: Article

DOI: 10.1002/CHIN.200138029 GOOGLE SCHOLAR

More publications in: ChemInform

Abstract

Addition of organolithium compounds to the carbonyl group ofcyclic ketones containing a Z-β-stannylvinyl moiety, e.g. (I) and (IV), proceedswith high remote stereocontrol from the same face on which the tin center istethered to furnish the adducts (III) and (VI), resp., as single diastereomers. Thereaction probably proceeds by chelation control. The reaction of cyclopentanonederivative (VII) containing a stannane directly bound to the ring with MeLi isnot stereoselective, while the larger allyllithium compounds (IX) react with highstereocontrol. The allyl inversion observed for the addition of 2-butenyllithium(IXb) to compound (VII) points to an intramolecular reaction mechanism

Bibliographic References

  • Barbero, (2001), Angew. Chem., Int. Ed., 40, pp. 2101, 10.1002/1521-3773(20010601)40:11<2101::AID-ANIE2101>3.0.CO;2-H