The Journal of organic chemistry

Diastereoselective and intramolecular cycloadditions of asymmetric P-nitroso phosphine oxides

RW Ware, CS Day, SB King

Index: Ware Jr., Roy W.; Day, Cynthia S.; King, S. Bruce Journal of Organic Chemistry, 2002 , vol. 67, # 17 p. 6174 - 6180

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Citation Number: 21

Abstract

Benzyl phenyl P-nitroso phosphine oxide (5) reacts as an NO heterodienophile with 1, 3- cyclopentadiene to give the diastereomeric cycloadducts 6a, b in a ratio of 1.5: 1 (6a: 6b). The same reaction in the presence of tin tetrachloride produces 6a, b in a ratio of 2.9: 1 (6a: 6b). Cycloaddition of the structurally modified P-nitroso phosphine oxide (18) with 1, 3- cyclopentadiene forms the diastereomeric cycloadducts 16a, b in a ratio of 3.1: 1 (16a: ...