Synthesis of Functionalized Medium-Sized trans-Cycloalkenes by 4π Electrocyclic Ring Opening/Alkylation Sequence

Tomohiro Ito; Masaki Tsutsumi; Ken-Ichi Yamada; Hiroshi Takikawa; Yousuke Yamaoka; Kiyosei Takasu

doi:10.1002/anie.201906665

Synthesis of Functionalized Medium-Sized trans-Cycloalkenes by 4π Electrocyclic Ring Opening/Alkylation Sequence

Angew Chem Int Ed Engl. 2019 Aug 19;58(34):11836-11840. doi: 10.1002/anie.201906665. Epub 2019 Jul 24.

Authors

Tomohiro Ito¹, Masaki Tsutsumi¹, Ken-Ichi Yamada^{1

2}, Hiroshi Takikawa¹, Yousuke Yamaoka¹, Kiyosei Takasu¹

Affiliations

¹ Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto, 606-8501, Japan.
² Current address: Graduate School of Pharmaceutical Sciences, Tokushima University, Shomachi, Tokushima, 770-8505, Japan.

PMID: 31259460
DOI: 10.1002/anie.201906665

Abstract

Development of a novel synthetic method for medium-sized trans-cycloalkenes (TCAs) is described. Functionalized TCAs are readily prepared from simple cycloalkanones in a few steps, namely, enol silyl ether formation, [2+2] cycloaddition, and domino 4π electrocyclic ring opening/alkylation (conjugate addition). The first example of central-to-planar chirality transfer from enantiomerically enriched cyclobutenes to TCAs is also described.

Keywords: cycloalkenes; electrocyclic reactions; medium-sized rings; planar chirality; synthetic methods.

Publication types

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

Abstract

Publication types

Grants and funding