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An observation of diastereoface selectivity in thermal reactions between δ-alkoxyallylstannanes and aldehydes

✍ Scribed by Simon V Mortlock; Eric J Thomas

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
230 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

The 6-alkoxyallylstannanes (4) and ( 5) react stereoselectively on heating with e-nitrobenzaldehyde to provide the homoallylic alcohols ( 14) -( 17), with (14) : (15) = 82 : 18; (16) : (17) = 73 : 27.

The chemistry of allylstannanes has been widely investigated over the last few years, and their reactions with aldehydes developed into useful, stereoselective procedures for the synthesis of homoallylic alcohols.' Of particular interest is the dependence of the stereoselectivity of these reactions upon the reaction conditions. Thus on heating with aldehydes, the (E)-crotylstannane (1; X -H) reacts to give anti-products (2; X = H),* whereas under Lewis acid catalysed conditions, w-products (3; X -H) are formed,' and a-substituted allylstannanes (1; X = Me, OR) provide anti,cis-products (2) on heating with -aldehydes, and w,trans-products (3; X = Me) under Lewis acid catalysed conditions.'

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1,5-Asymmetric induction in reactions be
1,5-Asymmetric induction in reactions betweenδ-alkoxyallylstannanes and aldehydes induced by tin (IV) chloride
✍ Alan H. McNeill; Eric J. Thomas 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 245 KB

## Treatment of (S)-4-benzyloxypent-(2E)-enyl(tributyl)stannane (3) with tin (IV) chloride at -78 OC, followed by the addition of an aldehyde, gives Ij-diol derivatives (6) with excellent 1 J-diastereoselectiviry. Allylstannanes undergo stereoselective reactions with aldehydes to give homoahylic a

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## Abstract The hydrophobic effect in the reaction of a homoallyl alcohol with an aldehyde (__Yadav__'s reaction system) under aqueous conditions in the presence of an acidic surfactant was studied indicating the presence of the alkyl‐substituent effect, although not a dramatic one. The DBSA‐promot