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Allylation of aldehydes and imines: promoted by reuseable polymer-supported sulfonamide of N-glycine.
Org Lett. 2006 Feb 16; 8(4):633-6.OL

Abstract

[reaction: see text] A allylation of aldehydes and imines (generated in situ from aldehydes and amines) with allyltributyltin promoted by recoverable and reusable the polymer-supported sulfonamide of N-glycine has been developed. Good to high yields were obtained in various cases. Most of the SnBu(3) residue can be recovered as Bu(3)SnCl. Highly stereoselective synthesis of N-Boc-(2S,3S)-3-hydroxy-2-phenylpiperidine 7 was achieved by using the P4a-mediated allylation of Boc-l-phenylglycinal as a key step.

Authors+Show Affiliations

Li GL
Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 FengLin Lu, Shanghai 200032, China.
Zhao G
No affiliation info available

MeSH

AldehydesCatalysisGlycineIminesMolecular StructureOrganotin CompoundsPiperidinesPolymersStereoisomerismSulfonamides

Pub Type(s)

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

Language

eng

PubMed ID

16468729

Citation

Li, Gui-long, and Gang Zhao. "Allylation of Aldehydes and Imines: Promoted By Reuseable Polymer-supported Sulfonamide of N-glycine." Organic Letters, vol. 8, no. 4, 2006, pp. 633-6.
Li GL, Zhao G. Allylation of aldehydes and imines: promoted by reuseable polymer-supported sulfonamide of N-glycine. Org Lett. 2006;8(4):633-6.
Li, G. L., & Zhao, G. (2006). Allylation of aldehydes and imines: promoted by reuseable polymer-supported sulfonamide of N-glycine. Organic Letters, 8(4), 633-6.
Li GL, Zhao G. Allylation of Aldehydes and Imines: Promoted By Reuseable Polymer-supported Sulfonamide of N-glycine. Org Lett. 2006 Feb 16;8(4):633-6. PubMed PMID: 16468729.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Allylation of aldehydes and imines: promoted by reuseable polymer-supported sulfonamide of N-glycine. AU - Li,Gui-long, AU - Zhao,Gang, PY - 2006/2/14/pubmed PY - 2006/11/10/medline PY - 2006/2/14/entrez SP - 633 EP - 6 JF - Organic letters JO - Org Lett VL - 8 IS - 4 N2 - [reaction: see text] A allylation of aldehydes and imines (generated in situ from aldehydes and amines) with allyltributyltin promoted by recoverable and reusable the polymer-supported sulfonamide of N-glycine has been developed. Good to high yields were obtained in various cases. Most of the SnBu(3) residue can be recovered as Bu(3)SnCl. Highly stereoselective synthesis of N-Boc-(2S,3S)-3-hydroxy-2-phenylpiperidine 7 was achieved by using the P4a-mediated allylation of Boc-l-phenylglycinal as a key step. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16468729/Allylation_of_aldehydes_and_imines:_promoted_by_reuseable_polymer_supported_sulfonamide_of_N_glycine_ DB - PRIME DP - Unbound Medicine ER -