Catalytic enantioselective aza-Diels–Alder reactions of unactivated acyclic 1,3-dienes with aryl-, alkenyl-, and alkyl-substituted imines,Chemical Communications

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Catalytic enantioselective aza-Diels–Alder reactions of unactivated acyclic 1,3-dienes with aryl-, alkenyl-, and alkyl-substituted imines
Chemical Communications ( IF 4.3 ) Pub Date : 2017-07-19 00:00:00 , DOI: 10.1039/c7cc03010j
Yasuo Hatanaka _{1,

2,

3,

4} , Shuuto Nantaku _{1,

2,

3,

4} , Yuhki Nishimura _{1,

2,

3,

4} , Tomoyuki Otsuka _{1,

2,

3,

4} , Tohru Sekikaw _{1,

2,

3,

4}

Affiliation

A catalytic enantioselective aza-Diels–Alder reaction of unactivated acyclic dienes with aryl-, alkenyl-, and alkyl-substituted imines is described. With 5–10 mol% loadings of a new Brønsted acid catalyst, the aza-Diels–Alder reaction of unactivated acyclic dienes proceeded to give the corresponding aza-Diels–Alder adducts in high yields (up to 98%) with excellent enantioselectivity (up to 98% ee). Preliminary DFT calculations suggest that the reaction proceeds through a chiral ion pair intermediate.

中文翻译：

未活化的无环1,3-二烯与芳基，烯基和烷基取代的亚胺的催化对映选择性氮杂-Diels-Alder反应

描述了未活化的无环二烯与芳基，烯基和烷基取代的亚胺的催化对映选择性氮杂-Diels-Alder反应。在新布朗斯台德酸催化剂的负载量为5-10 mol％的情况下，未活化的无环二烯的aza-Diels-Alder反应以高收率（高达98％）得到相应的aza-Diels-Alder加合物，具有出色的对映选择性（高达到98％ee）。初步的DFT计算表明该反应通过手性离子对中间体进行。

更新日期：2017-07-28

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