Highly Chemoselective Synthesis of Purino[3,2-c]oxazoles via the Asymmetric Dearomative [3+2] Cycloaddition of Purines with Donor–Acceptor Oxiranes DOI

Meng‐Cheng Zhang,

Dong‐Chao Wang, Hai‐Ting Wang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(41), P. 7527 - 7532

Published: Oct. 7, 2022

A Ni(II)/bisoxazoline-catalyzed asymmetric dearomative [3+2] cycloaddition of substituted purines with donor–acceptor oxiranes was developed. This reaction, which proceeds via highly chemoselective C–C bond cleavage the oxiranes, accesses chiral purino[3,2-c]oxazole compounds (≤99% ee after enrichment crystallization). The electronic effects purine ring determine reactivity substrate. general applicability this method illustrated by gram-scale synthesis, diverse transformations product, and promising biological activities selected derivatives.

Language: Английский

Highly Chemoselective Synthesis of Purino[3,2-c]oxazoles via the Asymmetric Dearomative [3+2] Cycloaddition of Purines with Donor–Acceptor Oxiranes DOI

Meng‐Cheng Zhang,

Dong‐Chao Wang, Hai‐Ting Wang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(41), P. 7527 - 7532

Published: Oct. 7, 2022

A Ni(II)/bisoxazoline-catalyzed asymmetric dearomative [3+2] cycloaddition of substituted purines with donor–acceptor oxiranes was developed. This reaction, which proceeds via highly chemoselective C–C bond cleavage the oxiranes, accesses chiral purino[3,2-c]oxazole compounds (≤99% ee after enrichment crystallization). The electronic effects purine ring determine reactivity substrate. general applicability this method illustrated by gram-scale synthesis, diverse transformations product, and promising biological activities selected derivatives.

Language: Английский

Citations

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