Stereoselective multimodal transformations of planar chiral 9-membered diallylic amides

Katsuhiko Tomooka; Masaki Suzuki; Maki Shimada; Runyan Ni; Kazuhiro Uehara

doi:10.1021/ol202009x

Stereoselective multimodal transformations of planar chiral 9-membered diallylic amides

Org Lett. 2011 Sep 16;13(18):4926-9. doi: 10.1021/ol202009x. Epub 2011 Aug 23.

Authors

Katsuhiko Tomooka¹, Masaki Suzuki, Maki Shimada, Runyan Ni, Kazuhiro Uehara

Affiliation

¹ Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga-shi, Fukuoka 816-8580, Japan. ktomooka@cm.kyushu-u.ac.jp

PMID: 21861490
DOI: 10.1021/ol202009x

Abstract

Intermolecular reactions of planar chiral 9-membered diallylic amides provide a variety of bicyclic compounds with central chiralities in a stereospecific fashion with high group selectivity. Lewis-acid-promoted intramolecular reactions of the obtained bicyclic compounds provide transannular products in a stereospecific fashion. Furthermore, a direct transannular reaction of diallylic amide involving sequential intermolecular-intramolecular reactions has been developed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemical synthesis
Amides / chemistry*
Molecular Structure
Stereoisomerism

Substances

Amides