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. Issue 16 (16th October 2014)

• Record Type: Journal Article
• Authors: Kim, Ko Hoon; Lim, Jin Woo; Lee, Junseung; Go, Min Jeong; Kim, Jae Nyoung
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 16(2014)
• Page Start: 3363
• Page End: 3369
• Publication Date: 2014-10-16
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201400571
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh2ch46rg5" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>