120312-94-9Relevant academic research and scientific papers
Mukaiyama aldol addition to α-chloro-substituted aldehydes. Origin of the unexpected syn selectivity
Borg, Tessie,Danielsson, Jakob,Somfai, Peter
, p. 1281 - 1283 (2010)
The addition of sterically demanding enolsilanes to α-chloro aldehydes results unexpectedly in preferential formation of the anti-PFA product (1,2-syn), while the addition of the corresponding boron enolate furnishes the expected polar Felkin-Anh product
Diastereoselective nucleophilic addition to aldehydes with polar α- And α,β-substituents
Borg, Tessie,Danielsson, Jakob,Mohiti, Maziar,Restorp, Per,Somfai, Peter
supporting information; experimental part, p. 2022 - 2036 (2011/10/31)
The stereoselectivities obtained in Lewis acid-promoted Mukaiyama aldol additions and Sakurai allylations of mono-, and syn- and anti-disubstituted aldehydes possessing various polar α- and β-substituents under non-chelating conditions are presented. The
Studies in marine macrolide synthesis: Synthesis of the C1-C15 subunit of spongistatin 1 (altohyrtin A) and 15,16-anti aldol coupling reactions
Paterson, Ian,Oballa, Renata M.
, p. 8241 - 8244 (2007/10/03)
The C1-C15 aldehyde 3, containing the AB-spiroacetal of spongistatin 1 (1), was prepared in 17 steps from methyl ketone (S)-8. The C15 and C16 stereocentres could be introduced together, relying on Felkin-Anh control, by using a boron-mediated, anti aldol coupling reaction, as in 22 → 25 and 26.
