Journal article
Stereochemical Aspects of Aldehyde Additions to Cyclohex-2-Enylstannanes
Australian Journal of Chemistry, Vol.38(12), pp.1767-1777
1985
Abstract
Cyclohex-2-enylation of aldehydes, mediated with boron trifluoride etherate, involves γ-equatorial approach of the presumed aldehyde-Lewis acid adduct (RCHO-BF3), irrespective of starting stannane stereochemistry. Marginal threo selectivity characterizes homoallyl alcohol formation from benzaldehyde, whereas alkanals react with high erythro selectivity, so that 1-(1′-hydroxyalkyl)cyclohex-2-enes in this diastereomeric form are available based on allyltin chemistry.
Details
- Title
- Stereochemical Aspects of Aldehyde Additions to Cyclohex-2-Enylstannanes
- Authors
- David James Young (Author) - University of QueenslandW Kitching (Author) - University of Queensland
- Publication details
- Australian Journal of Chemistry, Vol.38(12), pp.1767-1777
- Publisher
- C S I R O Publishing
- Date published
- 1985
- DOI
- 10.1071/CH9851767
- ISSN
- 0004-9425
- Organisation Unit
- University of the Sunshine Coast, Queensland
- Language
- English
- Record Identifier
- 99449570202621
- Output Type
- Journal article
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