Highly efficient diastereoselective Exo Diels-Alder reactions of homochiral 2-(N-acylamino)-1-thia-1,3-dienes: A powerful entry into optically pure thiopyrans

Highly diastereoselective hetero-Diels–A

Highly diastereoselective hetero-Diels–Alder reaction of buta-1,3-diene with N-glyoxyloyl-(2R)-bornane-10,2-sultam: an efficient synthesis of homochiral (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate

✍ Małgorzata Kosior; Małgorzata Malinowska; Julita Jóźwik; Jean-Claude Caille; Jan 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 516 KB

The influence of Lewis acid on the diastereoselectivity of [4+2] cycloaddition of buta-1,3-diene to N-glyoxyloyl-(2R)bornane-10,2-sultam was investigated and high levels of asymmetric induction were achieved. (S)-3-[2-{(Methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate were