Atropisomeric Chiral Diiododienes (Z,Z)-2,3-Di(1-iodoalkylidene)tetralins: Synthesis, Enantiomeric Resolution, and Application in Asymmetric Catalysis

Masamichi Ogasawara; Hirotaka Sasa; Hao Hu; Yuta Amano; Hikaru Nakajima; Naoko Takenaga; Kiyohiko Nakajima; Yasuyuki Kita; Tamotsu Takahashi; Toshifumi Dohi

doi:10.1021/acs.orglett.7b01876

Atropisomeric Chiral Diiododienes (Z,Z)-2,3-Di(1-iodoalkylidene)tetralins: Synthesis, Enantiomeric Resolution, and Application in Asymmetric Catalysis

Org Lett. 2017 Aug 4;19(15):4102-4105. doi: 10.1021/acs.orglett.7b01876. Epub 2017 Jul 20.

Authors

Masamichi Ogasawara^{1

2}, Hirotaka Sasa³, Hao Hu^{1

2}, Yuta Amano³, Hikaru Nakajima², Naoko Takenaga⁴, Kiyohiko Nakajima⁵, Yasuyuki Kita⁶, Tamotsu Takahashi², Toshifumi Dohi³

Affiliations

¹ Department of Natural Science, Graduate School of Science and Technology, Tokushima University , Tokushima 770-8506, Japan.
² Institute for Catalysis and Graduate School of Life Science, Hokkaido University , Kita-ku, Sapporo 001-0021, Japan.
³ College of Pharmaceutical Sciences, Ritsumeikan University , 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.
⁴ Faculty of Pharmacy, Meijo University , 150 Yagotoyama, Tempaku-ku, Nagoya, 468-8503, Japan.
⁵ Department of Chemistry, Aichi University of Education , Igaya, Kariya, Aichi 448-8542, Japan.
⁶ Research Organization of Science and Technology, Ritsumeikan University , 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.

PMID: 28726416
DOI: 10.1021/acs.orglett.7b01876

Abstract

The C₂-symmetric tetralin-fused 1,4-diiodo-1,3-butadiene derivatives, (Z,Z)-2,3-di(1-iodoalkylidene)tetralin 1a-c, are atropisomeric and can be resolved into the two persistent axially chiral enantiomers by HPLC on a chiral stationary phase. The enantiomerically pure compounds can serve as chiral organocatalysts for dearomatizing spirolactonization to show good performance in up to 73% ee.

Publication types

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