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Bicyclic Lactams as Chiral Homoenolate Equivalents: Synthesis of (−)-Penienone

✍ Scribed by Waterson, Alex G.; Meyers, A. I.

Book ID
124075956
Publisher
American Chemical Society
Year
2000
Tongue
English
Weight
57 KB
Volume
65
Category
Article
ISSN
0022-3263

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✍ Jacob B. Schwarz; Paul N. Devine; A.I. Meyers 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 891 KB

Bicyclic Lactam 2 was transformed into a-cyanoenamine 8 in a four-step, high-yielding process. TMetalation of 8 was achieved using LiTMP in THFIHMPA, and the resultant homoenolate equivalent underwent stereoselective alkylation and subsequent hydrolysis to provide lactams of type 10 as a single dias