Tags

Type your tag names separated by a space and hit enter

Stereoselective vinylation of aryl N-(2-pyridylsulfonyl) aldimines with 1-alkenyl-1,1-heterobimetallic reagents.
Org Lett. 2011 Dec 16; 13(24):6464-7.OL

Abstract

Vinylation of aryl N-(2-pyridylsulfonyl) aldimines with versatile 1-alkenyl-1,1-borozinc heterobimetallic reagents is disclosed. In situ hydroboration of air-stable B(pin)-alkynes followed by chemoselective transmetalation with dimethylzinc and addition to aldimines provides B(pin)-substituted allylic amines in 53-93% yield in a one-pot procedure. The addition step can be followed by either B-C bond oxidation to provide α-amino ketones (71-98% yield) or Suzuki cross-coupling to furnish trisubstituted 2-arylated (E)-allylic amines (51-73% yield).

Links

PMC Free PDF
PMC Free Full Text

Authors+Show Affiliations

Hussain N
P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
Hussain MM
No affiliation info available
Ziauddin M
No affiliation info available
Triyawatanyu P
No affiliation info available
Walsh PJ
No affiliation info available

MeSH

AlkenesAlkynesCombinatorial Chemistry TechniquesIminesIndicators and ReagentsMolecular StructureOrganometallic CompoundsPyridinesStereoisomerismSulfonesZinc

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

22085226

Citation

Hussain, Nusrah, et al. "Stereoselective Vinylation of Aryl N-(2-pyridylsulfonyl) Aldimines With 1-alkenyl-1,1-heterobimetallic Reagents." Organic Letters, vol. 13, no. 24, 2011, pp. 6464-7.
Hussain N, Hussain MM, Ziauddin M, et al. Stereoselective vinylation of aryl N-(2-pyridylsulfonyl) aldimines with 1-alkenyl-1,1-heterobimetallic reagents. Org Lett. 2011;13(24):6464-7.
Hussain, N., Hussain, M. M., Ziauddin, M., Triyawatanyu, P., & Walsh, P. J. (2011). Stereoselective vinylation of aryl N-(2-pyridylsulfonyl) aldimines with 1-alkenyl-1,1-heterobimetallic reagents. Organic Letters, 13(24), 6464-7. https://doi.org/10.1021/ol202766g
Hussain N, et al. Stereoselective Vinylation of Aryl N-(2-pyridylsulfonyl) Aldimines With 1-alkenyl-1,1-heterobimetallic Reagents. Org Lett. 2011 Dec 16;13(24):6464-7. PubMed PMID: 22085226.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective vinylation of aryl N-(2-pyridylsulfonyl) aldimines with 1-alkenyl-1,1-heterobimetallic reagents. AU - Hussain,Nusrah, AU - Hussain,Mahmud M, AU - Ziauddin,Muhammed, AU - Triyawatanyu,Plengchat, AU - Walsh,Patrick J, Y1 - 2011/11/15/ PY - 2011/11/17/entrez PY - 2011/11/17/pubmed PY - 2012/2/22/medline SP - 6464 EP - 7 JF - Organic letters JO - Org Lett VL - 13 IS - 24 N2 - Vinylation of aryl N-(2-pyridylsulfonyl) aldimines with versatile 1-alkenyl-1,1-borozinc heterobimetallic reagents is disclosed. In situ hydroboration of air-stable B(pin)-alkynes followed by chemoselective transmetalation with dimethylzinc and addition to aldimines provides B(pin)-substituted allylic amines in 53-93% yield in a one-pot procedure. The addition step can be followed by either B-C bond oxidation to provide α-amino ketones (71-98% yield) or Suzuki cross-coupling to furnish trisubstituted 2-arylated (E)-allylic amines (51-73% yield). SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/22085226/Stereoselective_vinylation_of_aryl_N__2_pyridylsulfonyl__aldimines_with_1_alkenyl_11_heterobimetallic_reagents_ L2 - https://doi.org/10.1021/ol202766g DB - PRIME DP - Unbound Medicine ER -