1027074-75-4

Upstream product

• 155128-11-3 (1S,5R,3Z)-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-en-1-ol 
• 62-23-7 4-nitro-benzoic acid 
• 100-52-7 benzaldehyde 
• 155128-04-4 C₁₅H₃₀O₂S₂Si 
• 155128-03-3 Dithiocarbonic acid O-[(E)-(R)-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pent-2-enyl] ester S-methyl ester 
• 122749-21-7 (2E,4R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-2,4-dimethylpent-2-enoate 
• 124755-22-2 (2E,4R)-5-((tert-butyldimethylsilyl)oxy)-2,4-dimethylpent-2-en-1-ol 

Relevant academic research and scientific papers

Effective 1,5-, 1,6- and 1,7-remote stereocontrol in reactions of alkoxy- and hydroxy-substituted allylstannanes with aldehydes

Alk-2-enylstannanes with 4-, 5- and 6-alkoxy- or -hydroxy-substituents are transmetallated stereoselectively with tin(iv) halides to generate allyltin trihalides which react with aldehydes to give (Z)-alk-3-enols with useful levels of 1,5-, 1,6- and 1,7-stereocontrol. Alk-2-enylstannanes with a stereogenic centre bearing a hydroxy or alkoxy group at the 4-, 5- or 6-position, react with overall (Z)-1,5-, 1,6- and 1,7-syn-stereoselectivity with respect to the hydroxy and alkoxy substituents. The analogous reactions of alkoxy- and -hydroxyalk-2-enylstannanes with a methyl bearing stereogenic centre at the 4- or 5-position react with overall (Z)-1,5- and 1,6-anti-stereoselectivity with respect to the hydroxy and methyl substituents.

1,5-Asymmetric Induction in Lewis Acid-promoted Reactions of (5-Alkoxy-2,4-dimethylpent-2-enyl)tributylstannanes and Aldehydes

Allyltin trihalides generated in situ from (5-alkoxy-2,4-dimethylpent-2-enyl)tributylstannanes 8-10 and tin(IV) halides react with aldehydes with excellent 1,5-stereocontrol.