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- W2314862007 abstract "Diastereoisomerically pure (dr > 99:1) and enantiomerically enriched (er up to 98:2) substituted propargyl diols possessing a tertiary hydroxyl group were synthesized in a single-pot operation from simple acylsilanes through a combined catalytic enantioselective alkynylation of acylsilanes, followed by an allenyl-Zn-Brook rearrangement and Zn-ene-allene (or Zn-yne-allene) cyclization reaction. Two remarkable features of these reactions are the near complete transfer of chirality in the allenyl-Zn-Brook rearrangement and the highly organized six-membered transition state of the Zn-ene-allene carbocyclization found by DFT calculations. In this process, three new bonds and two new stereogenic centers are created in a single-pot operation in excellent diastereo- and enantiomeric ratios. DFT calculations show that the allenyl-Zn-Brook rearrangement occurs in preference to the classic [1,2]-Zn-Brook rearrangement owing to its significantly lower activation barrier." @default.
- W2314862007 created "2016-06-24" @default.
- W2314862007 creator A5007308411 @default.
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- W2314862007 creator A5075148080 @default.
- W2314862007 creator A5078090232 @default.
- W2314862007 creator A5088939758 @default.
- W2314862007 date "2014-10-22" @default.
- W2314862007 modified "2023-10-18" @default.
- W2314862007 title "Formation of Three New Bonds and Two Stereocenters in Acyclic Systems by Zinc-Mediated Enantioselective Alkynylation of Acylsilanes, Brook Rearrangement, and Ene-Allene Carbocyclization Reactions" @default.
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