Diastereoselective acyl nitroso Diels-Alder reactions using 1,3-dienes derived from (R)-4-tert-butyldimethylsilyloxy-2-cyclohexen-1-one

1,3-Dienes derived from (R)-4-t-butyldimethylsilyloxy-2-cyclohexen-1-one react with acyl nitroso die-nophiles to form exclusively anti [4 + 2] cycloaddition products. These regio and diastereoselective acyl nitroso Diels-Alder reactions increase the asymmetric complexity from one chiral center in the starting material to three chiral centers in the products in a single step and provide a powerful approach for the asymmetric synthesis of compounds containing 3,6-dihydro-1,2-oxazine structural feature.(c) 2023 Published by Elsevier Ltd.

Automated summary

1,3-Dienes derived from (R)-4-t-butyldimethylsilyloxy-2-cyclohexen-1-one react with acyl nitroso dienophiles to form exclusively anti [4 + 2] cycloaddition products. These regio and diastereoselective reactions increase the asymmetric complexity from one chiral center in the starting material to three chiral centers in the products in a single step, providing a powerful approach for the asymmetric synthesis of compounds containing 3,6-dihydro-1,2-oxazine structural feature.