Open AccessStereoselective Synthesis of trans-Decalin-Based Spirocarbocycles via Photocyclization of 1,2-Diketones
Author(s) -
Sijia Chen,
Zhang Zhong-chao,
Chongguo Jiang,
Chunbo Zhao,
Haojie Luo,
Jun Huang,
Zhen Yang
Publication year - 2021
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.1c02054
Subject(s) - decalin , stereocenter , intramolecular force , chemistry , stereoselectivity , density functional theory , stereochemistry , hydrogen bond , computational chemistry , organic chemistry , molecule , catalysis , enantioselective synthesis
Diastereoselective synthesis of the trans -decalin-based α-hydroxyl butanone spirocarbocycles bearing all-carbon quaternary stereogenic centers has been achieved via Norrish-Yang photocyclization of trans -decalin-substituted-2,3-butanediones using daylight. Density functional theory (DFT) calculations suggest that this diastereoselective reaction is affected by both substrate conformation and intramolecular hydrogen bonds. The developed chemistry could be applied to synthesizing the derivatives of the trans -decalin-based biologically important natural products.