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Efforts Toward a Unified Kainoid Family Synthesis Approach: Unexpected Sulfinamide‐Directed Conjugate Addition Results
Author(s) -
Chogii Isaac,
Das Pradipta,
Njardarson Jon T.
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800728
Subject(s) - chemistry , conjugate , stereocenter , intramolecular force , steric effects , sulfoxide , oxidizing agent , enantioselective synthesis , annulation , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , mathematical analysis , mathematics
A short asymmetric synthesis of an all‐ syn and all‐ trans kainoid core is reported. The synthetic route relies on the application of a new asymmetric [3+2] annulation reaction followed by a conjugate addition reaction to install this kainoid's three stereocenters. A surprising intramolecular conjugate addition enabled by the chiral tert ‐butylsulfinyl group residing on the 3‐pyrroline nitrogen atom surpassed its expected role as a steric spectator. Efforts to outcompete intramolecular 1,4‐addition by further oxidizing the sulfoxide, or use of additives, and advancement of the all‐ syn addition product to the requisite kainoid common core are detailed.