ja0571646_si_003.cif (17.06 kB)
Download fileDiastereoselective Diels−Alder Reactions of N-Sulfonyl-1-aza-1,3-butadienes with Optically Active Enol Ethers: An Asymmetric Variant of the 1-Azadiene Diels−Alder Reaction
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posted on 2006-03-01, 00:00 authored by Ryan C. Clark, Steven S. Pfeiffer, Dale L. BogerThe first detailed study of a room-temperature asymmetric Diels−Alder reaction of N-sulfonyl-1-aza-1,3-butadienes is reported enlisting a series of 19 enol ethers bearing chiral auxiliaries, with many
providing highly diastereoselective (endo and facial diastereoselection) reactions, largely the result of an
exquisitely organized [4+2] cycloaddition transition state. Three new, readily accessible, and previously
unexplored auxiliaries rationally emerged from the studies and provide remarkable selectivities (two of
these give 49:1 endo:exo and 48:1 facial selectivity) that promise to be useful in systems beyond those
detailed.