181948-09-4Relevant articles and documents
Enzymatic resolution of amines and amino alcohols using pent-4-enoyl derivatives
Takayama, Shuichi,Moree, Wilna J.,Wong, Chi-Huey
, p. 6287 - 6290 (1996)
Racemic amines and amino alcohols were enzymatically resolved by enantioselective acylation using cyanomethyl pent-4-enoate or by enantioselective enzymatic hydrolysis of the dipent-4-enoyl derivatives of amino alcohols to afford chiral pent-4-enamides wh
Stereochemical Control of Skeletal Diversity
Sello, Jason K.,Andreana, Peter R.,Lee, Daesung,Schreiber, Stuart L.
, p. 4125 - 4127 (2007/10/03)
(Equation presented) Substrates having appendages that pre-encode skeletal information (σ-elements) can be converted into products having distinct skeletons using a common set of reaction conditions. The sequential use of the Ugi 4CC-IMDA reaction, followed by allylation, hydrolysis, and acylation of a chiral amino alcohol appendage (σ-element), leads to substrates for a ROM/RCM or RCM reaction. The stereochemistry of the a-element and not its constitution controls the outcome of the pathway selected. This work illustrates the potential of linking stereochemical control to the challenging problem of skeletal diversity.