A domino sequence has been developed between vinyldiazoacetates and racemic allyl alcohols, involving five distinct steps. The sequence generates highly functionalized cyclopentanes with four new stereogenic centers as single diastereomers in 64-92% ee. The first step is a rhodium-catalyzed oxygen ylide formation, which is then followed by a [2,3]-sigmatropic rearrangement, an oxy-Cope rearrangement, a keto/enol tautomerization, and then finally a carbonyl ene reaction. With appropriate substrates, a further silyl deprotection and a 6-exo-trig cyclization can be added to the domino process.
A domino sequence has been developed between vinyldiazoacetates and racemic pan class="Chemical">allyl alcohols, involving five distinct steps. The sequence generates highly functionalized cyclopentanes with four new stereogenic centers as single diastereomers in 64-92% ee. The first step is a rhodium-catalyzed oxygen ylide formation, which is then followed by a [2,3]-sigmatropic rearrangement, an oxy-Cope rearrangement, a keto/enol tautomerization, and then finally a carbonyl ene reaction. With appropriate substrates, a further silyl deprotection and a 6-exo-trig cyclization can be added to the domino process.
Authors: Ming Yan; Neil Jacobsen; Wenhao Hu; Luisa S Gronenberg; Michael P Doyle; John T Colyer; Darren Bykowski Journal: Angew Chem Int Ed Engl Date: 2004-12-10 Impact factor: 15.336
Authors: Logan E Vine; Ryan D Reeves; Eleanor M Landwehr; Israel Fernández; Jennifer M Schomaker Journal: ACS Catal Date: 2021-07-15 Impact factor: 13.700