Asymmetric synthesis of enantio-enriched acyclic α-amino alkylstannanes and rearrangement behavior of carbanions thereof

Takahiro Tomoyasu, Katsuhiko Tomooka, Takeshi Nakai

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

An efficient stereocontrolled synthesis of enantio-enriched N-Boc-N-allyl-α-amino alkylstannanes and N,N-diallylic α-amino alkylstannanes starting from enantio-enriched α-hydroxy alkylstannane has been developed. The aza-Wittig rearrangement of enantio-defined N,N-diallyl-α-amino alkyllithium, generated by tin-lithium exchange, is shown to proceed predominantly with inversion of configuration at the Li-bearing carbon terminus.

Original languageEnglish
Pages (from-to)1239-1242
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number6
DOIs
Publication statusPublished - Feb 3 2003

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Bearings (structural)
Tin
Lithium
Carbon

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Asymmetric synthesis of enantio-enriched acyclic α-amino alkylstannanes and rearrangement behavior of carbanions thereof. / Tomoyasu, Takahiro; Tomooka, Katsuhiko; Nakai, Takeshi.

In: Tetrahedron Letters, Vol. 44, No. 6, 03.02.2003, p. 1239-1242.

Research output: Contribution to journalArticle

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