Novel synthetic approach to nine-membered diallylic amides: Stereochemical behavior and utility as chiral building block

Katsuhiko Tomooka, Masaki Suzuki, Kazuhiro Uehara, Maki Shimada, Toshiyuki Akiyama

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

An efficient approach to nine-membered diallylic cyclic amides having a variety of substituents has been developed. The synthesized amides have stable planar chirality at ambient temperature. The transformation of the enantiomerically enriched amides provides optically active compounds containing stereogenic centers in a stereospecific fashion. As a demonstration of the synthetic utility of the amides, we have synthesized (+)-γ-lycorane using such an optically active amide as a chiral building block.

Original languageEnglish
Pages (from-to)2518-2522
Number of pages5
JournalSynlett
Issue number16
DOIs
Publication statusPublished - Oct 1 2008

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Amides
Chirality
Demonstrations
Temperature

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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Novel synthetic approach to nine-membered diallylic amides : Stereochemical behavior and utility as chiral building block. / Tomooka, Katsuhiko; Suzuki, Masaki; Uehara, Kazuhiro; Shimada, Maki; Akiyama, Toshiyuki.

In: Synlett, No. 16, 01.10.2008, p. 2518-2522.

Research output: Contribution to journalArticle

Tomooka, Katsuhiko ; Suzuki, Masaki ; Uehara, Kazuhiro ; Shimada, Maki ; Akiyama, Toshiyuki. / Novel synthetic approach to nine-membered diallylic amides : Stereochemical behavior and utility as chiral building block. In: Synlett. 2008 ; No. 16. pp. 2518-2522.
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