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Substituent Effect on Diastereoselectivity in Photochemistry of Valerophenone
Bong Ser Park*,Sungsu Cho,Sang-Hyuk Chong 대한화학회 2007 Bulletin of the Korean Chemical Society Vol.28 No.7
Valerophenone shows a dramatic shift of photoreactivity by a cyclopropyl group at alpha position to the carbonyl group. By the minor change of structure, the diastereoselectivity of the Yang photocyclization is reversed and the ratio of cyclization to elimination products increases significantly.
High Diastereoselectivity in the Yang Photocyclization via Remote Hydrogen Abstraction Reaction
장미,박봉서 대한화학회 2016 Bulletin of the Korean Chemical Society Vol.37 No.9
1-Benzoyl-1-(o-alkoxyphenyl)cyclopropanes undergo Yang photocyclization to form dihydrobenzo-pyranols in a stereospecific manner. The cyclopropyl group at alpha position to carbonyls gives not only a bias in the most stable geometries of the starting ketones but also conformational restriction on geometries of biradical intermediates. More importantly, intramolecular hydrogen bonds seem to give an additional effect on conformational control of the biradical reactivity.
Substituent Effect on Diastereoselectivity in Photochemistry of Valerophenone
Park, Bong-Ser,Cho, Sung-Su,Chong, Sang-Hyuk Korean Chemical Society 2007 Bulletin of the Korean Chemical Society Vol.28 No.7
Valerophenone shows a dramatic shift of photoreactivity by a cyclopropyl group at alpha position to the carbonyl group. By the minor change of structure, the diastereoselectivity of the Yang photocyclization is reversed and the ratio of cyclization to elimination products increases significantly.
Li, Qing Ri,Dong, Guang Ri,Park, Sook Jin,Hong, Yong Rae,Kim, In Su,Jung, Young Hoon WILEY‐VCH Verlag 2013 European journal of organic chemistry Vol.2013 No.20
<P><B>Abstract</B></P><P>A concise asymmetric formal synthesis of (–)‐swainsonine from readily available <SMALL>D</SMALL>‐erythronolactone is described. The key steps include a highly diastereoselective amination of a chiral benzylic ether, which occurs with the retention of stereochemistry using chlorosulfonyl isocyanate, and a palladium‐catalyzed decarboxylative <I>N</I>‐allylation of an allyl carbamate.</P>