EventsThe 4th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-4-01875
This submission belongs to the session a. General Organic Synthesis of the event The 4th International Electronic Conference on Synthetic Organic Chemistry
Published date
11 Sep, 2000
Citation
Massimo Zorzi, Gerhard Lascober, Kevin J. Hodgetts, Studies Towards New Reagents for Asymmetric Hydroboration: Synthesis of Racemic Trans-2,5-diisopropylborolane, in Proceedings of The 4th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2000, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-4-01875
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Studies Towards New Reagents for Asymmetric Hydroboration: Synthesis of Racemic Trans-2,5-diisopropylborolane

Kevin J. Hodgetts 1
Gerhard Lascober 1
Massimo Zorzi 1
1. Department of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland
Abstract
The cyclic hydroboration of 2,7-dimethyl-2,6-octadiene was studied. It was found that the stereochemical outcome of the reaction was dependent upon the solvent, temperature, time, and the nature of the borane reagent. Monobromoborane in carbon tetrachloride at 76 oC gave after 8 hr a 4:1 mixture of trans:cis-2,5-diisopropylborolane. Pure racemic trans-2,5-diisopropyl borolane was isolated following selective complexation of the cis-2,5-diisopropylborolane with 1-(2-hydroxyethyl)-pyrrolidine.
Keywords
n/a
Lewis Acid Catalyzed Enantioselective Reactions Using Highly Coordinating Nucleophiles. Conjugate Additions of Thiols, Thiocarboxylic acids, and O-Benzylhydroxylamine
Enantioselective hydride abstraction in organic substrates: future applications for chiral carbenium ions