Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase

Azusa Kondoh; Masafumi Oishi; Tadahiro Takeda; Masahiro Terada

doi:10.1002/anie.201508178

Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase

Angew Chem Int Ed Engl. 2015 Dec 21;54(52):15836-9. doi: 10.1002/anie.201508178. Epub 2015 Oct 20.

Authors

Azusa Kondoh¹, Masafumi Oishi², Tadahiro Takeda³, Masahiro Terada^{4

5}

Affiliations

¹ Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan).
² Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan).
³ Process Technology Research Laboratories, Daiichi Sankyo Co., Ltd, Edogawa-ku, Tokyo 134-8630 (Japan).
⁴ Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan). mterada@m.tohoku.ac.jp.
⁵ Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan). mterada@m.tohoku.ac.jp.

PMID: 26480953
DOI: 10.1002/anie.201508178

Abstract

A chiral bis(guanidino)iminophosphorane catalyzes enantioselective addition reactions of a 1,3-dithiane derivative as a pronucleophile. The chiral uncharged organosuperbase facilitates the addition of benzyloxycarbonyl-1,3-dithiane to aromatic N-Boc-protected imines to provide optically active α-amino-1,3-dithiane derivatives, which are valuable versatile building blocks in organic synthesis.

Keywords: 1,3-dithianes; asymmetric catalysis; organocatalysis; organosuperbases; phosphazenes.

Publication types

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