Auxiliary-directed peroxidation of 1, 4-dienes

PH Dussault, TA Anderson, MR Hayden, KJ Koeller…

Index: Dussault, Patrick H.; Anderson, Todd A.; Hayden, Michael R.; Koeller, Kevin J.; Jason Niu Tetrahedron, 1996 , vol. 52, # 38 p. 12381 - 12398

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Citation Number: 4

Abstract

The addition of singlet oxygen (1O2) to the proximal alkene of auxiliary-tethered 1, 4-dienes and the addition of triplet oxygen (3O2) to the proximal position of the corresponding pentadienyl radicals both produce conjugated diene hydroperoxides in moderate to high diastereomeric excess. Negligible stereoselection is observed for additions of 1O2 to the distal alkene of Z, Z-heptadienes due to the lack of control of alkene conformation. Despite ...