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Stereoselective synthesis of spiro[tetrahydropyran-3,3'-oxindole] derivatives employing Prins cascade strategy.
Org Lett. 2014 Dec 19; 16(24):6267-9.OL

Abstract

A variety of aldehydes undergo smooth coupling with 4-hydroxy-N-methyl-2-methylene-N-phenylbutanamide in the presence of BF3·OEt2 under ambient conditions to produce the corresponding spiro-oxindole derivatives in good yields with excellent selectivity. It is an entirely new strategy to construct the spirocycles in a one-pot operation through a Prins cascade process.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Reddy BV
Natural Product Chemistry, ‡Centre for Chemical Biology, §Laboratory of Crystallography, and ⊥Centre for Nuclear Magnetic Resonance and Structural Chemistry, CSIR-Indian Institute of Chemical Technology , Tarnaka, Hyderabad 500 607, India.
Swathi V
No affiliation info available
Swain M
No affiliation info available
Bhadra MP
No affiliation info available
Sridhar B
No affiliation info available
Satyanarayana D
No affiliation info available
Jagadeesh B
No affiliation info available

MeSH

AldehydesBoranesCatalysisCyclizationIndolesMolecular StructureOxindolesPhenylbutyratesSpiro CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

25485939

Citation

Reddy, B V Subba, et al. "Stereoselective Synthesis of Spiro[tetrahydropyran-3,3'-oxindole] Derivatives Employing Prins Cascade Strategy." Organic Letters, vol. 16, no. 24, 2014, pp. 6267-9.
Reddy BV, Swathi V, Swain M, et al. Stereoselective synthesis of spiro[tetrahydropyran-3,3'-oxindole] derivatives employing Prins cascade strategy. Org Lett. 2014;16(24):6267-9.
Reddy, B. V., Swathi, V., Swain, M., Bhadra, M. P., Sridhar, B., Satyanarayana, D., & Jagadeesh, B. (2014). Stereoselective synthesis of spiro[tetrahydropyran-3,3'-oxindole] derivatives employing Prins cascade strategy. Organic Letters, 16(24), 6267-9. https://doi.org/10.1021/ol503089m
Reddy BV, et al. Stereoselective Synthesis of Spiro[tetrahydropyran-3,3'-oxindole] Derivatives Employing Prins Cascade Strategy. Org Lett. 2014 Dec 19;16(24):6267-9. PubMed PMID: 25485939.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective synthesis of spiro[tetrahydropyran-3,3'-oxindole] derivatives employing Prins cascade strategy. AU - Reddy,B V Subba, AU - Swathi,V, AU - Swain,Manisha, AU - Bhadra,Manika Pal, AU - Sridhar,B, AU - Satyanarayana,D, AU - Jagadeesh,B, Y1 - 2014/12/08/ PY - 2014/12/9/entrez PY - 2014/12/9/pubmed PY - 2015/8/22/medline SP - 6267 EP - 9 JF - Organic letters JO - Org Lett VL - 16 IS - 24 N2 - A variety of aldehydes undergo smooth coupling with 4-hydroxy-N-methyl-2-methylene-N-phenylbutanamide in the presence of BF3·OEt2 under ambient conditions to produce the corresponding spiro-oxindole derivatives in good yields with excellent selectivity. It is an entirely new strategy to construct the spirocycles in a one-pot operation through a Prins cascade process. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25485939/Stereoselective_synthesis_of_spiro[tetrahydropyran_33'_oxindole]_derivatives_employing_Prins_cascade_strategy_ DB - PRIME DP - Unbound Medicine ER -
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