Stereoselective Synthesis of Alcohols, XXIX. Addition of (α‐Methoxycrotyl)boronates to Aldehydes
- 1 May 1989
- journal article
- Published by Wiley in European Journal of Inorganic Chemistry
- Vol. 122 (5) , 903-909
- https://doi.org/10.1002/cber.19891220519
Abstract
α‐Phenoxy‐ (4) and α‐methoxycrotylboronates (8) were obtained from the α‐chlorocrotylboronates 1. Addition of the phenoxy compound to aldehydes gave the homoallyl alcohols 5/6 as Z/E mixtures; addition of the methoxy compound 8 led to essentially pure Z‐enol ethers 9. Enantiomerically enriched (ca. 90% e.e.) 8 was used in reactions with chiral aldehydes to ensure the formation of the new stereogenic centers under reagent control of diastereoselectivity.Keywords
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