Asymmetric construction of quaternary centers by enantioselective allylation: application to the synthesis of the serotonin antagonist LY426965

  • Org Lett. 2002 May 30;4(11):1951-3. doi: 10.1021/ol025971t.
Scott E Denmark  1 ,  Jiping Fu
Affiliations
  • 1. Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. [email protected]
PMID: 12027655 DOI: 10.1021/ol025971t
Abstract

[reaction: see text] Catalytic enantioselective allylation with a chiral bisphosphoramide was applied to the synthesis of LY426965, a serotonin antagonist. The key step, addition of a 3,3-disubstituted allyltrichlorosilane to benzaldehyde, provided the adduct containing a stereogenic quaternary center with excellent diastereoselectivity and enantioselectivity.

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