Asymmetric 1,4-Dihydroxylation of 1,3-Dienes by Catalytic Enantioselective Diboration
- 8 June 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 131 (26), 9134-9135
- https://doi.org/10.1021/ja809610h
Abstract
Asymmetric 1,4-dihydroxylations of 1,3-dienes, and other transformations, are initiated by the Pt-catalyzed enantioselective addition of bis(pinacolato)diboron (B2(pin)2) to conjugated dienes. The studies reported in this communication suggest that both cyclic and acyclic substrates will participate in this reaction; however, dienes which are unable to adopt the S-cis conformation are unreactive. For most substrates, 1,4-addition is the predominant pathway. In addition to oxidation to the derived 2-buten-1,4-diol, stereoselective carbonyl allylation with the intermediate bis(boronate) ester is also described.Keywords
This publication has 36 references indexed in Scilit:
- Enantioselective Synthesis of γ-Hydroxyenones by Chiral Base-Catalyzed Kornblum DeLaMare RearrangementJournal of the American Chemical Society, 2006
- A Biomimetically Inspired, Efficient Synthesis of the South 7 Hemisphere of Cephalostatin 7Journal of the American Chemical Society, 2005
- Advances in singlet oxygen chemistryTetrahedron, 2005
- Biomimetic Synthesis of Elysiapyrones A and BOrganic Letters, 2005
- Palladium‐Catalyzed 1,4‐Additions to Conjugated DienesPublished by Wiley ,2004
- Asymmetric Total Synthesis of (−)‐Nakadomarin AAngewandte Chemie-International Edition, 2004
- An enantioselective synthetic strategy toward the polyhydroxylated agarofuranTetrahedron Letters, 2001
- Enantioselective Total Synthesis of (−)-TaxolJournal of the American Chemical Society, 2000
- Studies Towards the Synthesis of Aplykurodins - Synthesis of 17,18-Dihydro-3,9-di-epi-aplykurodinone BEuropean Journal of Organic Chemistry, 2000
- Palladium(II)-catalyzed asymmetric 1,4-oxidation of 2-phenyl-1,3-cyclohexadieneTetrahedron Letters, 1997