A supramolecular "ship in bottle" strategy for enantiomeric selectivity in geminate radical pair recombination

被引：13

作者：

Poon, T

Turro, NJ

Chapman, J

Lakshminarasimhan, P

Lei, XG

Adam, W

Bosio, SG

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

[2] Columbia Univ, Dept Chem Engn, New York, NY 10027 USA

[3] Claremont Mckenna Coll, WM Keck Sci Ctr, Joint Sci Dept, Claremont, CA 91711 USA

[4] Pitzer Coll, WM Keck Sci Ctr, Joint Sci Dept, Claremont, CA 91711 USA

[5] Scripps Coll, WM Keck Sci Ctr, Joint Sci Dept, Claremont, CA 91711 USA

[6] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 12期

关键词：

D O I：

10.1021/ol034362y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions in which zeolites are modified with chiral inductors to serve as media for chiral induction are often limited by the propensity of both substrate and inductor to occupy the same supercage. Herein, we report a "ship in bottle" strategy utilizing the thermal decomposition of dioxetanes obtained from oxazolidinone-substituted enecarbamates for the enantioselective generation of methyl desoxybenzoin (MDB). Photoexcitation of the supramolecular geminate molecular pair results in enrichment of the opposite enantiomer of MDB.

引用

页码：2025 / 2028

页数：4

共 25 条

[1] Highly diastereoselective dioxetane formation in the photooxygenation of enecarbamates with an oxazolidinone chiral auxiliary: Steric control in the [2+2] cycloaddition of singlet oxygen through conformational alignment [J].