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Enantio- and Diastereoselective Synthesis of a 3,4-Divinylpyrrolidine via Asymmetric Deprotonation and Cyclization of a 9-Chloro-5-aza-2,7-nonadiene

✍ Scribed by Alexander Deiters; Birgit Wibbeling; Dieter Hoppe

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
76 KB
Volume
343
Category
Article
ISSN
1615-4150

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✦ Synopsis

Scheme 1. Synthesis of the cyclization precursor 1. (a) 4-Bromobut-2-enoic acid methyl ester (2.2 equiv., E/Z = 80 : 20), K 2 CO 3 (1.5 equiv.), 80 °C; (b) DIBAH (1.5 equiv.), hexane/THF, ±78 °C; (c) NaH (0.25 equiv.), 6 (0.25 equiv.), THF, 60 °C; (d) LiCl (4.0 equiv.), n-BuLi (1.3 equiv.), CH 3 SO 2 Cl (2.0 equiv.), THF, ±78 °C ® rt

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