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Stereodivergent Synthesis of N-Heterocycles by Catalyst-Controlled, Activity-Directed Tandem Annulation of Diazo Compounds with Amino Alkynes.
Angew Chem Int Ed Engl. 2015 Oct 26; 54(44):12962-7.AC

Abstract

A stereodivergent synthesis of five-membered N-heterocycles, such as 2,3-dihydropyrroles, and 2-methylene and 3-methylene pyrrolidines, has been developed through a tandem annulation of amino alkynes with diazo compounds and involves the trapping of in situ formed intermediates. Mechanistic investigations indicate that the copper-catalyzed tandem annulations proceed by allenoate formation and subsequent intramolecular hydroamination. In contrast, the rhodium-catalyzed protocol features a carbenoid insertion into the NH bond and subsequent Conia-ene cyclization.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Liu K
School of Pharmaceutical Engineering & Life Science, Changzhou University, Changzhou 213164 (China).
Zhu C
School of Pharmaceutical Engineering & Life Science, Changzhou University, Changzhou 213164 (China).
Min J
School of Pharmaceutical Engineering & Life Science, Changzhou University, Changzhou 213164 (China).
Peng S
School of Pharmaceutical Engineering & Life Science, Changzhou University, Changzhou 213164 (China).
Xu G
School of Pharmaceutical Engineering & Life Science, Changzhou University, Changzhou 213164 (China).
Sun J
School of Pharmaceutical Engineering & Life Science, Changzhou University, Changzhou 213164 (China). jtsun08@gmail.com.

MeSH

AlkynesAzo CompoundsCatalysisCopperHeterocyclic CompoundsMolecular StructureOrganometallic CompoundsStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26350164

Citation

Liu, Kai, et al. "Stereodivergent Synthesis of N-Heterocycles By Catalyst-Controlled, Activity-Directed Tandem Annulation of Diazo Compounds With Amino Alkynes." Angewandte Chemie (International Ed. in English), vol. 54, no. 44, 2015, pp. 12962-7.
Liu K, Zhu C, Min J, et al. Stereodivergent Synthesis of N-Heterocycles by Catalyst-Controlled, Activity-Directed Tandem Annulation of Diazo Compounds with Amino Alkynes. Angew Chem Int Ed Engl. 2015;54(44):12962-7.
Liu, K., Zhu, C., Min, J., Peng, S., Xu, G., & Sun, J. (2015). Stereodivergent Synthesis of N-Heterocycles by Catalyst-Controlled, Activity-Directed Tandem Annulation of Diazo Compounds with Amino Alkynes. Angewandte Chemie (International Ed. in English), 54(44), 12962-7. https://doi.org/10.1002/anie.201507122
Liu K, et al. Stereodivergent Synthesis of N-Heterocycles By Catalyst-Controlled, Activity-Directed Tandem Annulation of Diazo Compounds With Amino Alkynes. Angew Chem Int Ed Engl. 2015 Oct 26;54(44):12962-7. PubMed PMID: 26350164.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereodivergent Synthesis of N-Heterocycles by Catalyst-Controlled, Activity-Directed Tandem Annulation of Diazo Compounds with Amino Alkynes. AU - Liu,Kai, AU - Zhu,Chenghao, AU - Min,Junxiang, AU - Peng,Shiyong, AU - Xu,Guangyang, AU - Sun,Jiangtao, Y1 - 2015/09/09/ PY - 2015/07/31/received PY - 2015/9/10/entrez PY - 2015/9/10/pubmed PY - 2016/4/22/medline KW - copper KW - cyclizations KW - diazo compounds KW - homogeneous catalysis KW - rhodium SP - 12962 EP - 7 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 54 IS - 44 N2 - A stereodivergent synthesis of five-membered N-heterocycles, such as 2,3-dihydropyrroles, and 2-methylene and 3-methylene pyrrolidines, has been developed through a tandem annulation of amino alkynes with diazo compounds and involves the trapping of in situ formed intermediates. Mechanistic investigations indicate that the copper-catalyzed tandem annulations proceed by allenoate formation and subsequent intramolecular hydroamination. In contrast, the rhodium-catalyzed protocol features a carbenoid insertion into the NH bond and subsequent Conia-ene cyclization. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/26350164/Stereodivergent_Synthesis_of_N_Heterocycles_by_Catalyst_Controlled_Activity_Directed_Tandem_Annulation_of_Diazo_Compounds_with_Amino_Alkynes_ DB - PRIME DP - Unbound Medicine ER -