Camphor sulfonyl hydrazines (CaSH) as organocatalysts in enantioselective Diels-Alder reactions.
Cyclic sulfonyl hydrazine was demonstrated for the first time as a new functionality for organocatalysis. A series of six-membered cyclic hydrazines derived from camphor sulfonic acid were synthesized. With trichloroacetic acid as cocatalyst, they are efficient organocatalysts for enantioselective Diels-Alder reactions with good chemical yields and up to 96% ee. The reactions took place in brine at 0 degrees C to room temperature.
He
Hao
H
Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, SAR, China.
Pei
Bao-Jian
BJ
Chou
Ho-Hsuan
HH
Tian
Tian
T
Chan
Wing-Hong
WH
Lee
Albert W M
AW
D002164:Camphor / Q000031:analogs & derivatives* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006572:Heterocyclic Compounds, Bridged-Ring / Q000737:chemistry*; D006834:Hydrazines / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D012492:Salts; D013237:Stereoisomerism
D006572:Heterocyclic Compounds, Bridged-Ring; D006834:Hydrazines; D012492:Salts; C017082:brine; C029424:hydrazine; D002164:Camphor