Allylsilane-interrupted homo-Nazarov cyclization and synthesis of bicyclo[3.2.1]octan-8-ones

作者：Yadav Veejendra K^*; Naganaboina Vijaya K; Hulikal Vijaykumar

来源：Tetrahedron Letters, 2014, 55(12): 2015-2018.

DOI：10.1016/j.tetlet.2014.02.018

• Cyclopropyl vinyl ketone
• Homo-Nazarov cyclization
• Oxyallyl cation
• Allylsilane
• Bicyclo[3.2.1]octan-8-one

The combination of homo-Nazarov cyclization of 2-(tert-butyldiphenylsilylmethyl)cyclopropyl vinyl ketone leading to oxyallyl cation and its subsequent [3+2] capture by allylsilane has been demonstrated as an useful strategy for the construction of functionalized bicyclo[3.2.1]octan-8-ones. The [3+2] capture proceeds exclusively in the exo mode to make the overall reaction diastereoselective. The less substituted end of the oxyallyl cation was found to react nearly two times faster than the more substituted end.

• 出版日期2014-3-19