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- W1998049555 abstract "Stereodefined alkenols prepared in two steps from a Weinreb amide derived from (R)-phenylglycinol undergo highly stereoselective Claisen rearrangements. The masked aldehyde moiety of the produced N-Boc-alkenyloxazolidines can then be recovered and reduced without epimerization, to yield new enantiopure chiral building blocks. Alternatively, epoxidation of these N-Boc-2-alkenyloxazolidines by a well-established intramolecular bromocarbamation involving the Boc protecting group occurs stereoselectively. The resulting α,β-epoxyoxazolidines are then transformed into trisubstituted stereodefined cyclopropanes. Claisen rearrangements of propargylic alcohols, on the other hand, stereoselectively give α-allenyloxazolidines. These compounds follow a different pathway to α-alkenyloxazolidines as regards bromocarbamation. An original route to enantiopure 3-hydroxy-4-phenylpiperidine was found in the course of this study." @default.
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- W1998049555 date "2002-01-01" @default.
- W1998049555 modified "2023-10-18" @default.
- W1998049555 title "Claisen Rearrangements of Allylic and Propargylic Alcohols Prepared by an N-Boc-2-acyloxazolidine Methodology − Application to the Synthesis of Original Chiral Building Blocks" @default.
- W1998049555 doi "https://doi.org/10.1002/1099-0690(20021)2002:1<29::aid-ejoc29>3.0.co;2-b" @default.
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