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Stereoselective Synthesis of Alcohols, XXIX. Addition of (α-Methoxycrotyl)boronates to Aldehydes

✍ Scribed by Hoffmann, Reinhard W. ;Dresely, Stefan

Publisher
Wiley (John Wiley & Sons)
Year
1989
Tongue
English
Weight
732 KB
Volume
122
Category
Article
ISSN
0009-2940

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✦ Synopsis

Reagent control of stereoselectivity / Z-Enol ether, formation of / Allylboronates, addition to aldehydes a C p h a O X p (4) & U-i.l&lOXy~O@bO~n8t& @) l b m the ccchtorocrotylboronates 1. Addith of the phenoxy compound to aldohydes gave the homoallyl alcohols !5/6 as Z/E mixtweq addition of the methoxy compound 8 led to mientidty pure 2 -1 ethers 9. Enantiomerically enriched (ca. 90% e.6.) 8 was used m reactioIIs with chiral aldehydes to ensure the formation of the new stereogenic centers under reagent control of

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Stereoselective synthesis of alcohols, XXXV. Addition ofE- andZ-crotylboronates to chiral α-substituted aldehydes
✍ Brinkmann, Heinrich ;Hoffmann, Reinhard W. 📂 Article 📅 1990 🏛 Wiley (John Wiley & Sons) 🌐 English ⚖ 714 KB

Allylboration reaction / Asymmetric induction / Calculations, force-field / Transition-state models The direction (Cramlanti-Cram) and the extent of asymmetric induction on addition of crotylboronates to a range of chiral aldehydes was investigated. A reversal in the sense of the asymmetric inducti

Stereoselective Synthesis of Alcohols, X
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Both the (Z)-and the (E)-y-alkoxy-substituted allylboronates 1 and 3 have been prepared. They add to aldehydes with a diastereoselectivity generally exceeding 90% to give the syn-(2) and anti-diol derivatives 4, respectively. The structure of one of these adducts has been established by conversion i