Novel synthons from mucochloric acid: the first use of alpha,beta-dichloro-gamma-butenolides and gamma-butyrolactams for direct vinylogous aldol addition.
Novel 5-(1'-hydroxy)-gamma-butyrolactone and gamma-butyrolactam subunits were synthesized by direct vinylogous aldol addition of alpha,beta-dichloro gamma-butyrolactones and gamma-butyrolactams with aldehydes under basic conditions. Different bases and solvents were screened in the context of generating gamma-butyrolactones. Diastereoselectivity was observed and gamma-butenolides and gamma-butyrolactams showed opposite diastereoselectivity under the same reaction condition.
Das Sarma
Koushik
K
Research API, Pfizer Global Research & Development, Ann Arbor Laboratories, Pfizer, Inc., 2800 Plymouth Road, Ann Arbor, Michigan 48105, USA.
Zhang
Ji
J
Curran
Timothy T
TT
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D005663:Furans / Q000737:chemistry*
D000447:Aldehydes; D005663:Furans; C014117:mucochloric acid; C116609:3-hydroxybutanal; C004511:butenolide; D015107:4-Butyrolactone