Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
1.1.4.2.5.4 Intermolecular Triple Domino Michael/Michael/Aldol Reactions

DOI: 10.1055/sos-SD-204-00032

Mase, N.Science of Synthesis: Asymmetric Organocatalysis, (20121206.

Triple domino reactions of the three components propanal, cinnamaldehyde, and alkenes 270 proceed via an organocatalytic Michael/Michael/aldol sequence, affording the cyclohexene derivatives 271 bearing four stereogenic centers with excellent enantioselectivities in good to moderate yields.[‌282‌,‌284‌,‌285‌] These products can be used as building blocks in organic synthesis. The process consists of an enamine-based Michael reaction followed by an iminium-based Michael reaction and an enamine-based aldol condensation reaction (Scheme 61). Similar domino Michael/Michael/aldol reactions[‌184‌,‌186‌,‌286‌‌291‌] and other triple domino reactions[‌292‌] have also been reported.

Meeeee 88 Meeeeeeeeeeeee Meeeee Meeeee Meeeeee/Meeeeee/Meeee Meeeeeeee[‌888‌,‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M,8M,8M)-8-Meeeee-8-eeeee-8,8-eeeeeeeeeeeeeeee-8-eeeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee (M)-8-[eeeeeeee(eeeeeeeeeeeeeee)eeeeee]eeeeeeeeeee (88; 88ee, 8.88eeee) eee (M)-8-eeeee-8-eeeeeeeeeeee (8.8eeee, 8 eeeee) ee eeeeeee (8.8eM) eeee eeeee eeeee eeeeeeee MeMMM (8.8eeee, 8.8 eeeee) eee eeeeeeeeeeeeee (8.88eeee, 8.88 eeeee) ee 8°M. Meeee 8e, eee eeee eee eeeeeee ee eeeee ee, eee eeee eeeeeee eeeee eeeeeeee eeeeeeeeee ee eeeeeeee eeeeeeeee eee eeeeeeee (8888e, MM). Mee eeeeeee eee eeeeeeee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8 ee 8:8); eeeee: 88%; 88% ee; >88% ee.

References