Hydrazines camphor sulfonyl

Lee and co-workers reported camphor sulfonyl hydrazines 54 as organocatalysts in enantioselective Diels-Alder reactions of cyclopentadiene and a,[L-unsaturated aldehydes, Scheme 3.21 [34], On the other hand, a similar Diels-Alder cycloaddition reactions with camphor-derived sulfonylhydrazines and HC10 in MeNO were also developed by Langlois, et al. [35]. 

After the success of Macmillan s catalysts, other types of chiral amine were disclosed and applied in the FCA reaction as activators of a,(3-unsaturated aldehydes. Reports from a few groups have revealed that diaryIprolinol silyl ethers [11], camphor sulfonyl hydrazine [12], chiral aziridin-2-yl methanols [13], and A-isopropylated bipyrrolidine [14] were efficient catalysts in the enantioselective alkylations of 4,7-dihydroindoles, 1-naphthols, and indoles. NEt3, benzoic acid, or... 

For chiral amine-catalyzed Diels-Alder reactions, a, 3-unsaturated ketones are a challenging class of dienophiles. With the use of a primary camphor sulfonyl hydrazine 60 as organocatalyst, Lee and coworkers successfully reaUzed asymmetric Diels-Alder reactions of a, 3-unsaturated ketones 27 (Scheme 38.17) [27]. 

Scheme 38.17 Camphor sulfonyl hydrazine catalyzed Diels-Alder reactions.

---