Enantioselective carbanion cyclization of 5-alkenyl carbamates induced by asymmetric lithiation with s-butyllithium/(-)-sparteine system

Katsuhiko Tomooka, Nobuyuki Komine, Tomoya Sasaki, Hideo Shimizu, Takeshi Nakai

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

Treatment of (E)-6-phenyl-5-hexenyl carbamates with s-BuLi/(-)-sparteine is shown to afford the trans-1,2-disubstituted cyclopentane derivatives in high % ee, along with the bicyclo[3.1.0]hexanes (bicyclization products).

Original languageEnglish
Pages (from-to)9715-9718
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number52
DOIs
Publication statusPublished - Dec 24 1998

Fingerprint

Sparteine
Cyclopentanes
Carbamates
Cyclization
Derivatives
butyllithium
bicyclo(3.1.0)hexane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Enantioselective carbanion cyclization of 5-alkenyl carbamates induced by asymmetric lithiation with s-butyllithium/(-)-sparteine system. / Tomooka, Katsuhiko; Komine, Nobuyuki; Sasaki, Tomoya; Shimizu, Hideo; Nakai, Takeshi.

In: Tetrahedron Letters, Vol. 39, No. 52, 24.12.1998, p. 9715-9718.

Research output: Contribution to journalArticle

Tomooka, Katsuhiko ; Komine, Nobuyuki ; Sasaki, Tomoya ; Shimizu, Hideo ; Nakai, Takeshi. / Enantioselective carbanion cyclization of 5-alkenyl carbamates induced by asymmetric lithiation with s-butyllithium/(-)-sparteine system. In: Tetrahedron Letters. 1998 ; Vol. 39, No. 52. pp. 9715-9718.
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