
Journal of Organic Chemistry p. 5141 - 5147 (1989)
Update date:2022-08-05
Topics:
Pearson, Anthony J.
Khetani, Vikram D.
Roden, Brian A.
The addition of chiral N-acyloxazolidinone enolates to diene-molybdenum and dienyl-iron complexes gives enantiomeric excesses as high as 80percent.The oxazolidinone derived from valinol adds preferentially to the pro-S terminus of the diene/dienyl complex while the oxazolidinone derived from norephedrine adds to the pro-R terminus.A rationalization of these experimental results is attempted based on Seebach's topological rules for the Michael addition of enamines to nitro olefins.
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Doi:10.1248/cpb.37.391
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