Enantioselective Diels-Alder reaction of α-(acylthio)acroleins: a new entry to sulfur-containing chiral quaternary carbons.
A catalytic and enantioselective Diels-Alder reaction of α-(carbamoylthio)acroleins induced by an organoammonium salt of chiral triamine is described. α-(Carbamoylthio)acroleins are designed and synthesized as new sulfur-containing dienophiles for the first time. The Diels-Alder reaction affords chiral tertiary thiol precursors with up to 91% ee.
EcoTopia Science Institute, Nagoya University, Chikusa, Nagoya 464-8603, Japan.
Akira
A
Sakakura
Hiroki
H
Yamada
Kazuaki
K
Ishihara
D000171:Acrolein / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*
D013438:Sulfhydryl Compounds; D013455:Sulfur; D002244:Carbon; D000171:Acrolein