Synthesis applications of cationic aza-Cope rearrangements. 16. Stereocontrolled synthesis of substituted cis-cyclopenta [b] pyrrolidines

…, ME Okazaki, EJ Jacobsen

Index: Overman, Larry E.; Okazaki, Mark E.; Jacobsen, E. Jon Journal of Organic Chemistry, 1985 , vol. 50, # 13 p. 2403 - 2405

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Citation Number: 20

Abstract

Reaction6 of l, 2-bis [(trimethylsilyl) oxy] cyclobutene (6) 7 with 1.1 equiv of benzyl (cyanomethyl) amine4* gave cyclobutanone 78 (IR 1790 cm-') in 75% yield (eq 2). The subsequent reaction of this intermediate with (l-phenylviny1) lithium (2.5 equiv,-78 OC, THF) occurred completely from the side opposite the dialkylamino group to provide a single adduct, 4a8 ('H NMR 6 3.68, AB q, JAB= 13.2 Hz, Av= 15.7 Hz, CH, CN; 3.6-3.8, m, CHN), ...