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Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams.
Org Lett. 2012 Nov 02; 14(21):5412-5.OL

Abstract

An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).

Authors+Show Affiliations

Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

23061465

Citation

Lv, Hui, et al. "Highly Enantioselective Addition of Enals to Isatin-derived Ketimines Catalyzed By N-heterocyclic Carbenes: Synthesis of Spirocyclic Γ-lactams." Organic Letters, vol. 14, no. 21, 2012, pp. 5412-5.
Lv H, Tiwari B, Mo J, et al. Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams. Org Lett. 2012;14(21):5412-5.
Lv, H., Tiwari, B., Mo, J., Xing, C., & Chi, Y. R. (2012). Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams. Organic Letters, 14(21), 5412-5. https://doi.org/10.1021/ol302475g
Lv H, et al. Highly Enantioselective Addition of Enals to Isatin-derived Ketimines Catalyzed By N-heterocyclic Carbenes: Synthesis of Spirocyclic Γ-lactams. Org Lett. 2012 Nov 2;14(21):5412-5. PubMed PMID: 23061465.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams. AU - Lv,Hui, AU - Tiwari,Bhoopendra, AU - Mo,Junming, AU - Xing,Chong, AU - Chi,Yonggui Robin, Y1 - 2012/10/12/ PY - 2012/10/16/entrez PY - 2012/10/16/pubmed PY - 2013/2/12/medline SP - 5412 EP - 5 JF - Organic letters JO - Org Lett VL - 14 IS - 21 N2 - An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee). SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23061465/Highly_enantioselective_addition_of_enals_to_isatin_derived_ketimines_catalyzed_by_N_heterocyclic_carbenes:_synthesis_of_spirocyclic_γ_lactams_ L2 - https://doi.org/10.1021/ol302475g DB - PRIME DP - Unbound Medicine ER -