Photocyclization reactions of cyclohexa- and cyclopenta-fused pyridinium salts. Factors governing regioselectivity.
The results of studies described in this report show that irradiation of 1,2-cyclopenta-fused pyridinium perchlorate in aqueous base promotes a remarkably regioselective photocyclization reaction that results in exclusive formation of a single tricyclic allylic alcohol. Moreover, transformation of this photoproduct to a spirocyclic amido diester followed by enzymatic desymmetrization produces an enantiomerically pure monoalcohol. This chemistry comprises a highly concise sequence for the preparation of what should become a useful synthon in synthetic organic chemistry.
Zhao
Zhiming
Z
Department of Chemistry, University of New Mexico, Albuquerque, New Mexico 87131, USA.
Duesler
Eileen
E
Wang
Canhui
C
Guo
Hua
H
Mariano
Patrick S
PS
D003500:Cyclization; D015394:Molecular Structure; D010472:Perchlorates / Q000737:chemistry* / Q000528:radiation effects; D010777:Photochemistry; D011726:Pyridinium Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D010472:Perchlorates; D011726:Pyridinium Compounds; D014867:Water