Formal Fluorinative Ring Opening of 2-Benzoylpyrrolidines Utilizing [1,2]-Phospha-Brook Rearrangement for Synthesis of 2-Aryl-3-fluoropiperidines

被引：18
|
作者：
Kondoh, Azusa [2 ]
Ojima, Rihaku [1 ]
Terada, Masahiro [1 ]
机构：
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Res & Analyt Ctr Giant Mol, Grad Sch Sci, Sendai, Miyagi 9808578, Japan
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 20期
关键词：
PHOSPHA-BROOK REARRANGEMENT; INTRAMOLECULAR CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; PIPERIDINES; REDUCTION; AMINATION; PYRIDINES; FUNCTIONALIZATION; AMINOFLUORINATION; AMINOCYCLIZATION;
D O I：
10.1021/acs.orglett.1c02907
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A ring expansion of 2-benzoylpyrrolidines, which involves the formal fluorinative ring opening utilizing the [1,2]-phospha-Brook rearrangement under Bronsted base catalysis and a subsequent intramolecular reductive amination, was developed. The operationally simple three-step protocol provides an efficient access to 2-aryl-3-fluoropiperidines. The methodology was further applied to the syntheses of azepanes and tetrahydroquinolines.
引用
收藏
页码：7894 / 7899
页数：6
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