Transition-metal-free oxidative cyclization of N-propargyl ynamides: stereospecific construction of linear polycyclic N-heterocycles,Green Chemistry

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Transition-metal-free oxidative cyclization of N-propargyl ynamides: stereospecific construction of linear polycyclic N-heterocycles
Green Chemistry ( IF 9.3 ) Pub Date : 2018-06-19 , DOI: 10.1039/c8gc01534a
Cai-Ming Wang _{1,

2,

3,

4,

5} , Lin-Jun Qi _{1,

2,

3,

4,

5} , Qing Sun _{1,

3,

4,

6,

7} , Bo Zhou _{1,

2,

3,

4,

5} , Zhi-Xin Zhang _{1,

2,

3,

4,

5} , Zai-Fa Shi _{1,

2,

3,

4,

5} , Shui-Chao Lin _{1,

2,

3,

4,

5} , Xin Lu _{1,

3,

4,

6,

7} , Lei Gong _{1,

2,

3,

4,

5} , Long-Wu Ye _{1,

2,

3,

4,

5}

Affiliation

An efficient NaBAr^F₄-catalyzed oxidative cascade cyclization of N-propargyl ynamides has been developed, where NaBAr^F₄ is demonstrated for the first time to be a highly effective catalyst for promoting such an oxidative cyclization. Importantly, this transition metal-free process strongly supports that this oxidative catalysis proceeds by a Lewis acid-catalyzed S_N2′ pathway, which is distinct from the related oxidative gold catalysis. This method leads to the efficient and practical synthesis of a diverse range of valuable polycyclic N-heterocycles with high diastereoselectivity and enantioselectivity by a chirality-transfer strategy.

中文翻译：

N-炔丙基甲酰胺的无过渡金属氧化环化：线性多环N-杂环的立体构型

已经开发了有效的NaBAr ^F₄催化的N-炔丙基炔酰胺的氧化级联环化，其中NaBAr ^F₄首次被证明是促进这种氧化环化的高效催化剂。重要的是，这种无过渡金属的过程有力地支持了这种氧化催化作用是通过路易斯酸催化的S _N 2'途径进行的，这不同于相关的氧化金催化作用。通过手性转移策略，该方法可有效，实用地合成具有高非对映选择性和对映选择性的各种有价值的多环N-杂环。

更新日期：2018-07-16

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