Diastereodivergent aldol reactions of beta-alkoxy ethyl ketones: modular access to (1,4)-syn and -anti polypropionates.
Asymmetric substrate-controlled aldol reactions of ethyl ketones of type 4 with aldehyde 3 are reported. Modular access to all possible syn- and anti-aldol products was obtained by careful choice of reaction conditions. To achieve good selectivities in this diastereodivergent approach, selection of the protective group on the beta-oxygen of the enolate (R (2)) was of critical importance.
Arikan
Fatih
F
University of Heidelberg, Department of Organic Chemistry, INF 270, 69120 Heidelberg, Germany.
Li
Jun
J
Menche
Dirk
D
D000447:Aldehydes / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D007659:Ketones; D011108:Polymers; D011422:Propionates; C116609:3-hydroxybutanal