Harvard College

Riken Corporation

Japan Science and Technology Corporation

Makoto Tokunaga

Eric N Jacobsen

Jay F Larrow

Yasuo Wakatsuki

The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic, chiral catalyst to produce a stereoisomerically- and/or regioisomerically-enriched product. The present invention also relates to hydrolytic kinetic resolutions of racemic and diastereomeric mixtures of epoxides.

Hydrolytic kinetic resolution of cyclic substrates

The invention provides processes for the preparation of fused pyrroles, preferably indoles, which permit the use of inexpensive aromatic amines themselves as the raw material and attain high atomic efficiency and high regioselectivity. Specifically, a process for the preparation of fused pyrroles, e.g., indoles bearing methyl at the 3-position of pyrrole ring and R(or R) of the general formula (4) at the 2-position thereof, or 3,3-disubstituted indoles bearing Rand Rat the 3-position of pyrrole ring and methyl at the 2-position thereof, characterized by reacting an alkynol of the general formula (4) with an aromatic primary amine in the presence of a ruthenium complex, more preferably with an acid or an ammonium salt thereof being made to coexist.[In the general formula (4), Rand Rare each independently hydrogen, optionally substituted alkyl, or optionally substituted aryl, or alternatively Rand Rmay be united to form an alkylene chain.]

Process for preparation of fused pyrroles

Nucleophilic kinetic resolution of cyclic substrates using silyl azides

Stereoselective ring opening reactions

Growing community of inventors

Wako, Japan

Makoto Tokunaga