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Photochemical Studies on 5‐Methylbicyclo[1.1.1]pentane Derivatives: p‐Orbital Overlap Controlled Enantioselectivity
Author(s) -
Ma Manling,
Yang Chao,
Li Bing,
Shao Yutian,
Zhao Guolei,
Xia Wujiong
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201100083
Subject(s) - chemistry , pentane , ketone , acetonitrile , photochemistry , bicyclic molecule , solid state , medicinal chemistry , organic chemistry
The first example of the p‐orbital overlap controlled enantioselectivity of Norrish type II photocyclization reaction was described. Irradiation of 5‐methyl bicyclo[1.1.1]pentanyl ketone with UV in the solid state as well as in the acetonitrile solution afforded the Norrish/Yang photocyclization compound as the sole product. Solid‐state asymmetric photochemical studies using ionic chiral auxiliary technique led to the enantioselectivity as high as 60%. The results were rationalized by X‐ray single crystal structure.
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