369651-19-4

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 369651-17-2 (1R,2S,5R)-1-((R)-1-methylallyl)menthol 
• 209251-28-5 (3S,4R)-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hex-5-en-3-ol 
• 304459-85-6 4-methyl-1-phenyl-hex-5-en-3-ol 
• 4894-61-5 trans-but-2-enyl chloride 
• 1229414-83-8 (4R,5R)-2-((R)-but-3-en-2-yl)-4,5-dicyclohexyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Highly (E)-selective BF3·Et2O-promoted allylboration of chiral nonracemic α-Substituted allylboronates and analysis of the origin of stereocontrol

(Figure presented) δ-Methyl-substituted homoallylic alcohols 2 were prepared in 71-88% yield, E:Z >30:1 and 93% to >95% ee via BF 3·Et2O-promoted allylboration with α-Me-allylboronate 1. The origin of high (E)-selectivity is proposed

Solid-phase synthesis of [5.5]-spiroketals

An efficient and reliable multi-step synthesis of 251 natural product-like [5.5]-spiroketals on solid supports has been developed. As central key step, a double intramolecular hetero-Michael (DIHMA) reaction to alkynones was applied. The sequence allows for introduction of numerous substituents on the scaffold and for variation of stereochemistry. [5.5]-Spiroketals bearing an additional ketone were obtained in high overall yields. Further diversification was achieved by reduction of the ketone and reductive amination using polymer-supported borohydride, Grignard reaction and conversion to oxime derivatives in the solution phase.

Racemization in prins cyclization reactions

Isotopic labeling experiments were performed to elucidate a new mechanism for racemization in Prins cyclization reactions. The loss in optical activity for these reactions was shown to occur by 2-oxonia-Cope rearrangements by way of a (2)-oxocarbenium ion

Stereoselective synthesis of the tetrahydropyran core of polycarvernoside A

(Chemical Equation Presented) A concise and stereoselective synthesis of the tetrasubstituted tetrahydropyran core of polycavernoside A was achieved in 55% overall yield from 3-benzyloxypropanal. A stereoselective allyl transfer reaction was used in the synthesis of enol ether 18 followed by a TFA-mediated cyclization to create the three new asymmetric centers in the tetrahydropyran with complete stereocontrol in a single-pot process.

Highly enantioselective alk-2-enylation of aldehydes through an allyl-transfer reaction

Enantiopure homoallylic alcohols such as 1 (conveniently prepared from alk-2-enyl metal reagents with (-)- or (+)-menthone) serve as alk-2-enyl donors to aldehydes. The allyl-transfer reaction, which proceeds via a chairlike six-membered-ring transition s

New and stereoselective synthesis of 1,4-disubstituted buten-4-ols (homoallylic alcohol α-adducts) from the corresponding γ-isomers (3,4-disubstituted buten-4-ols) via an acid-catalyzed allyl-transfer reaction with aldehydes

The γ-adducts of homoallylic alcohols 3, derived from aldehydes via the usual reaction with common allylic metals 1, were converted to the corresponding α-adducts 6 by an acid-catalyzed allyl-transfer reaction. In the allyl-transfer reaction, anti-and syn