897943-05-4Relevant articles and documents
Bis(oxazoline) lewis acid catalyzed aldol reactions of pyridine N-oxide aldehydes-synthesis of optically active 2-(1-hydroxyalkyl)pyridine derivatives: Development, scope, and total synthesis of an indolizine alkaloid
Landa, Aitor,Minkkilae, Anna,Blay, Gonzalo,Jergensen, Karl Anker
, p. 3472 - 3483 (2006)
A new. short, and simplified procedure for the synthesis of optically active pyridine derivatives from prochiral pyridine-N-oxides is presented. The catalytic and asymmetric Mukaiyama aldol reaction between ketene silyl acetals and l-oxypyridine-2-carhaldehyde derivatives catalyzed by chiral copper(ii)-bis(oxazoline) complexes gave optically active 2-(hydroxyalkyl)-and 2-(anti-1.2-dihydroxyalkyl)pyridine derivatives in good yields and diastereoselectivities, and in excellent enantioselectivities - up to 99% enantiomeric excess. As a synthetic application of the developed method, a full account for the asymmetric total synthesis of a nonnatural indolizine alkaloid is provided.