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Chiral N,N'-dioxide/Mg(OTf)₂ complex-catalyzed asymmetric [2,3]-rearrangement of in situ generated ammonium salts.

ABSTRACT: Catalytic enantioselective [2,3]-rearrangements of in situ generated ammonium ylides from glycine pyrazoleamides and allyl bromides were achieved by employing a chiral N,N'-dioxide/Mg^II complex as the catalyst. This protocol provided a facile and efficient synthesis route to a series of anti-α-amino acid derivatives in good yields with high stereoselectivities. Moreover, a possible catalytic cycle was proposed to illustrate the reaction process and the origin of stereoselectivity.

SUBMITTER: Lin Q

PROVIDER: S-EPMC8157646 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Chiral N,N'-dioxide/Mg(OTf)2 complex-catalyzed asymmetric [2,3]-rearrangement of in situ generated ammonium salts.

Lin Qianchi Q Hu Bowen B Xu Xi X Dong Shunxi S Liu Xiaohua X Feng Xiaoming X

Chemical science 20200219 11

Catalytic enantioselective [2,3]-rearrangements of in situ generated ammonium ylides from glycine pyrazoleamides and allyl bromides were achieved by employing a chiral N,N'-dioxide/MgII complex as the catalyst. This protocol provided a facile and efficient synthesis route to a series of anti-α-amino acid derivatives in good yields with high stereoselectivities. Moreover, a possible catalytic cycle was proposed to illustrate the reaction process and the orig ...[more]

PMID: 34122811

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