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Synthesis and diastereoselective Diels–Alder reactions of homochiral C2-symmetric butane-1,2-diacetal-based 1,3-dienes

✍ Scribed by Bruno Linclau; Philip J. Clarke; Mark E. Light

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
365 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

The C 2 -symmetric, butane diacetal (BDA) auxiliary-based dienes 2 and 3 are described, which display moderate to excellent diastereoselectivities in Diels-Alder reactions with a range of dienophiles under thermal and Lewis acid-catalysed conditions.

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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