Diastereoconvergent Synthesis of Chiral Diarylmethyl Sulfones by Direct Sulfonylation of Diarylmethanols Diastereomixtures with Sodium Sulfinates Catalyzed by SnBr2

被引：11

作者：

Yamamoto, Hiroshi ^{[1
]}

Nakata, Kenya ^{[1
]}

机构：

[1] Shimane Univ, Grad Sch Nat Sci & Technol, Dept Chem, 1060 Nishikawatsu, Matsue, Shimane 6908504, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 30期

关键词：

Carbocations; Chiral auxiliaries; Diastereoselectivity; Sulfonylation; Tin; ALPHA-ARYLATION; BOND FORMATION; FACILE ACCESS; CHEMISTRY; ALCOHOLS; SUBSTITUTION; ALKYLATION;

D O I：

10.1002/ejoc.201900830

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthetic method affording a variety of chiral diarylmethyl sulfones was developed via diastereoconvergent sulfonylation of diarylmethanols diastereomixtures bearing a chiral auxiliary with sodium sulfinates using a SnBr2 catalyst and trimethylsilyl chloride (TMSCl) under mild reaction conditions. The reaction proceeded in a diastereoconvergent pattern via a diarylmethycation intermediate. The chiral auxiliary induced high diastereoselectivity and improved reactivity.

引用

页码：4906 / 4910

页数：5

共 7 条

[1] Chiral-Auxiliary-Controlled Diastereoconvergent Benzamidation Reactions of Diastereomixtures of Diarylmethanols with Benzamide Catalyzed by SnBr4
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[2] Chiral Inductive Diastereoconvergent Friedel-Crafts Alkylation Reaction of Diastereomixtures of Diarylmethanols with 2-Naphthol Derivatives Catalyzed by SnBr4
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[6] Copper(II)-Catalyzed Direct Sulfonylation of C(sp2)-H Bonds with Sodium Sulfinates
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[7] Iodine/TBHP-Promoted One-Pot Deoxygenation and Direct 2-Sulfonylation of Quinoline N-Oxides with Sodium Sulfinates: Facile and Regioselective Synthesis of 2-Sulfonylquinolines
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