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Stereoselective synthesis of diastereomeric atropisomeric lactam with various ring sizes and their structural characterization

✍ Scribed by Osamu Kitagawa; Masao Fujita; Mitsuteru Kohriyama; Hiroshi Hasegawa; Takeo Taguchi

Book ID: 104211157
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 125 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01608-7

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✦ Synopsis

Diastereomeric atropisomeric N-ortho-tert-butylphenyl lactams with ring sizes from four to seven were prepared with high diastereoselectivity through an aminocyclization reaction. In the case of four-and five-membered ring formation, thermodynamically stable atropisomeric lactams having a trans-relationship between the ortho-tert-butyl group and the C-4 or C-5 substituent were obtained, while in the sixand seven-membered ring-forming reaction, cis-atropisomeric lactams, kinetic controlled products, were exclusively isolated.

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