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Enantioselective Synthesis of 2-Methyl-1,2-syn- and 2-Methyl-1,2-anti-3-Butenediols Via Allene Hydroboration-Aldehyde Allylboration Reaction Sequences

The hydroboration of allene 7 with ((d)Ipc)(2)BH at 0 °C provides the kinetic allylborane 12Z with ≥20 : 1 selectivity. However, when the hydroboration is performed at 85 °C, the kinetically formed allylborane isomerizes to give the thermodynamic allylborane 12E with ≥12 : 1 selectivity. Subsequent...

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Bibliographic Details
Main Authors: Chen, Ming, Handa, Masaki, Roush, William R.
Format: Artigo
Language:Inglês
Published: 2009
Subjects:
Online Access:https://ncbi.nlm.nih.gov/pmc/articles/PMC2762002/
https://ncbi.nlm.nih.gov/pubmed/19778012
https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1021/ja904599h
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