## Abstract The stereochemical course of the intramolecular allylsilaneβaldehyde condensation of **1a** has been investigated. A modest preference for the product arising from a synclinal orientation of double bonds was observed with __Lewis__βacid catalysts. Cyclization induced by fluoride ion res
Stereochemistry of allylmetal-aldehyde condensations. 2. Allylstannanes
β Scribed by Denmark, Scott E.; Weber, Eric J.
- Book ID
- 126969550
- Publisher
- American Chemical Society
- Year
- 1984
- Tongue
- English
- Weight
- 282 KB
- Volume
- 106
- Category
- Article
- ISSN
- 0002-7863
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The high pressure (9 kbar, 3oOC) mediated addition of benzaldehyde to allylstannane (1) occurs stereospecifically with syn approach of the electrophile. At 6OoC, the reaction is less selective, probably due to some isomerization of cis (1) to trun.s (1). At both temperatures good erythro diastexeose
enolsilanes 1 does not govern the stereochemistry of aldol condensation products. We recently reported for the first time', acetals la6'8, that compounds 2, structural analogous of add to aldehydes and Schiff bases in a cross-aldol type condensation, to afford B-hydroxyacids and B-Lactams respective