Abstract
A tandem [4+2]/[3+2]-cycloaddition of nitroalkenes tethered to α,β-unsaturated ester dipolarophiles can be effectively triggered with a vinyl ether. Using the chiral vinyl ether 6 as the dienophile, nitroalkenes 1 and 2 undergo highly selective tandem cycloaddition. Hydrogenolytic cleavage of the resulting nitroso acetals produce α-hydroxy lactams (-)-14 and (-)-21 in >98% e.e. with excellent recovery of the chiral auxiliary. The high diastereoselectivity is seen to arise from a strong endo preference for the vinyl ether together with an intrinsic facial bias in the auxiliary.
Original language | English (US) |
---|---|
Pages (from-to) | 4857-4876 |
Number of pages | 20 |
Journal | Tetrahedron |
Volume | 46 |
Issue number | 13-14 |
DOIs | |
State | Published - 1990 |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry