Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase.
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.
Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan).
Azusa
A
Kondoh
Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan).
Masafumi
M
Oishi
Process Technology Research Laboratories, Daiichi Sankyo Co., Ltd, Edogawa-ku, Tokyo 134-8630 (Japan).
Tadahiro
T
Takeda
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.|Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan). mterada@m.tohoku.ac.jp.
Masahiro
M
Terada
1,3-dithianes; asymmetric catalysis; organocatalysis; organosuperbases; phosphazenes