Proline-based N-oxides as readily available and modular chiral catalysts. Enantioselective reactions of allyltrichlorosilane with aldehydes.
[reaction: see text]. A proline-based N-oxide is identified that serves as an effective catalyst for the reaction of allyltrichlorosilane with aryl and alpha,beta-unsaturated aldehydes at room temperature to afford the desired homoallylic alcohols in up to 92% ee. The chiral catalyst can be easily prepared from optically pure proline in three simple steps and 60% overall yield.
Traverse
John F
JF
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Zhao
Yu
Y
Hoveyda
Amir H
AH
Snapper
Marc L
ML
D000438:Alcohols / Q000032:analysis / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003497:Cyclic N-Oxides / Q000737:chemistry*; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D000438:Alcohols; D000447:Aldehydes; D003497:Cyclic N-Oxides; D012821:Silanes; D011392:Proline