期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 352, 期 13, 页码 2142-2146出版社
WILEY-BLACKWELL
DOI: 10.1002/adsc.201000438
关键词
asymmetric Diels-Alder reaction; camphor sulfonyl hydrazine; CaSH; hydrazines; organocatalysis
资金
- Faculty Research Grants [FRG1/08-09/058, FRG2/09-10/039]
- Hong Kong Research Grant Council
- Nagoya University
In one step, the well known chiral auxiliary, Oppolzer's camphor sultam, is turned into the new generation camphor sulfonyl hydrazine (CaSH II) organocatalyst. With the primary hydrazine functionality external to the tricyclic structure, CaSH II is active towards ketone substrates in asymmetric Diels-Alder reactions. The iminium intermediate of the catalytic cycle was isolated. When it was put back into the solution reaction system, the same level of yield and stereoselectivity was observed. Based on these observations, we argue that organocatlyst is actually an in situ chiral auxiliary.
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