.png){kind=icon}
.png){kind=icon}
Return
Selective Synthesis of Polycyclic 2-Oxaspiro[5.5]undecanones and Diaryl Allylic Alcohols From Propargyl Benzyl Ethers Using an NXS–Water System
.png){kind=icon}
PRE
AI
B
S
S
DOI：10.1002/ajoc.70476.png)
.png){kind=icon}
Original request for help.png){kind=icon}
Share.png){kind=icon}
Save
Abstract
En 中文
Herein, we report an approach for the selective construction of 2-oxaspiro[5.5]undecan-9-ones as well as 3,3-diaryl allylic alcohols by employing propargyl-benzyl ethers in N-halosuccinimide-water (NXS-H2O) system. This methodology shows a broad substrate scope for propargyl-benzyl ethers, resulting in a selective construction of a structurally divergent library of 2-oxaspiro[5.5]undecan-9-ones, when employed (2:1) CH3CN: H2O and NXS reagents. Further, it was extended for the construction of bis-spiro systems as well. By tuning the conditions to (50:1) CH3CN: H2O, we could also selectively promote the migration of e-rich arenes to obtain the corresponding 3,3-diarylallylic alcohols. In the case of trimethoxy-arene (migrating group), a selective formation of benzo[c]oxepanes was observed via an intramolecular iodo-cyclization through 7-endo-dig fashion.
Keywords:
2-oxaspiro[5.5]undecanes
benzo[c]oxepanes
cationic [1, 5]-aryl migrations
phenonium ions
propargylic-benzyl ethers
Journal
IF:
2.7
Papers:
938
Citations:
6.5K
Organization
Cited Papers