Thermal Intramolecular [2+2] Cycloaddition: Synthesis of 3-Azabicyclo[3.1.1]heptanes from Morita-Baylis-Hillman Adduct-Derived 4,4-Diaryl-1,3-dienes

• Published in: Advanced synthesis & catalysis Vol. 356; no. 16; pp. 3363 - 3369
• Main Authors: Kim, Ko Hoon, Lim, Jin Woo, Lee, Junseung, Go, Min Jeong, Kim, Jae Nyoung
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 03-11-2014; WILEY‐VCH Verlag
• Subjects: 3-azabicyclo[3.1.1]heptanes; 3-azabicyclo[3.2.0]heptanes; Bearing; Catalysis; Derivatives; intramolecular [2+2] cycloaddition; Morita-Baylis-Hillman adducts; Synthesis
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201400571

Various 3‐azabicyclo[3.1.1]heptane derivatives were synthesized from Morita–Baylis–Hillman adduct‐derived 1,3‐dienes bearing a 4,4‐diaryl moiety through a thermal intramolecular [2+2] cycloaddition approach. By using the same approach, bicyclo[3.1.1]heptane, 3‐azabicyclo[3.2.0]heptane, and 3‐oxabicyclo[3.1.1]heptane derivatives could also be synthesized. A structurally similar dimethylallyl derivative underwent an intramolecular ene reaction to afford the pyrrolidine derivative.