✦ LIBER ✦

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

✍ Scribed by Małgorzata Kosior; Małgorzata Malinowska; Julita Jóźwik; Jean-Claude Caille; Janusz Jurczak

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 516 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(02)00746-2

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✦ Synopsis

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 synthesized in 15% overall yield, applying as a crucial step the above-mentioned [4+2] cycloaddition catalyzed by ZnBr 2 .