Synthesis of Optically Pure 3,3′-Diaryl Binaphthyl Disulfonic Acids via Stepwise N-S Bond Cleavage

被引：17

作者：

Hatano, Manabu ^{[1
]}

Ozaki, Takuya ^{[1
]}

Nishikawa, Keisuke ^{[1
]}

Ishihara, Kazuaki ^{[1
,2
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

[2] Nagoya Univ, CREST, Japan Sci & Technol Agcy JST, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 20期

关键词：

NUCLEOPHILIC-SUBSTITUTION; PARA-TOLUENESULFONYL; SECONDARY-AMINES; DEPROTECTION; REAGENT; ARENESULFONAMIDES; SULFONAMIDES; ALKYLATION; REDUCTION; INDOLES;

D O I：

10.1021/jo401848z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed a practical synthesis of optically pure 3,3 '-diaryl-1,1 '-binaphthyl-2,2 '-disulfonic acids (i.e., (R)- or (S)-3,3 '-Ar-2-BINSAs) from the parent chiral sulfonimides via stepwise N-S bond cleavage of the sulfonimides and the resultant sulfonamides. This unusual synthesis, which provides arylsulfonic acids from arylsulfonamides, is valuable since common methods particularly give amines with the decomposition of sulfone groups during deprotection.

引用

页码：10405 / 10413

页数：9

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