Catalytic Enantioselective Aza Diels–Alder Reactions of Imino Dienophiles

✍ Scribed by Sulan Yao; Mogens Johannsen; Rita G. Hazell; Karl Anker Jørgensen

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 119 KB
• Volume: 37
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/(sici)1521-3773(19981204)37:22<3121::aid-anie3121>3.0.co;2-j

✦ Synopsis

1 mol% of catalyst is sufficient: The hetero Diels-Alder reaction of α-imino esters 1 with activated conjugated dienes 2 (R=H, Me) needs only 1 mol% of a 2,2'-bis(diarylphosphanyl)-1,1'-binaphthyl (BINAP) copper(I) complex as the catalyst to generate the adducts 3 in good yields and with enantioselectivities up to 96%. The reaction can also be carried out on gram scale! Tos=H CC H SO ; TMS=Me Si.