对称2-吡啶酮光二聚体的亲电重排导致的不对称性。

Asymmetry by electrophilic rearrangement of symmetric 2-pyridone photodimers.

作者信息

Lim Yeon-Hee, Li Tindy, Chen Peiling, Schreiber Patrick, Kuznetsova Larissa, Carroll Patrick J, Lauher Joseph W, Sieburth Scott McN

机构信息

Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794, USA.

出版信息

Org Lett. 2005 Nov 24;7(24):5413-5. doi: 10.1021/ol052071e.

DOI:10.1021/ol052071e

PMID:16288519

Abstract

[reaction: see text] Halogenation of achiral trans-2-pyridone photodimers results in 1,3-migration of an amide nitrogen and formation of a chiral structure with six stereogenic centers and well-differentiated functionality. The reactivity of this product toward nucleophiles, including the allylic halide, is dominated by participation by the amide nitrogen.

摘要

[反应：见正文] 非手性反式-2-吡啶酮光二聚体的卤化反应导致酰胺氮的1,3-迁移，并形成具有六个立体中心和良好区分功能的手性结构。该产物对亲核试剂（包括烯丙基卤化物）的反应活性主要由酰胺氮参与决定。