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Catalyst control in sequential asymmetric allylic substitution: stereodivergent access to N,N-diprotected unnatural amino acids.
J Org Chem. 2011 Jul 01; 76(13):5495-501.JO

Abstract

The sequential use of Cu-catalyzed asymmetric allylic alkylation, olefin cross-metathesis, and Ir-catalyzed asymmetric allylic amination allows the concise, stereodivergent synthesis of complex chiral amines with complete regiocontrol and good diastereoselectivity, exemplified by the synthesis of a pair of diastereoisomeric unnatural branched amino acid derivatives.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Tosatti P
School of Chemistry, University of Leeds, LS2 9JT Leeds, UK.
Campbell AJ
No affiliation info available
House D
No affiliation info available
Nelson A
No affiliation info available
Marsden SP
No affiliation info available

MeSH

AlkylationAllyl CompoundsAminationAmino AcidsCatalysisCopperIridiumMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21563816

Citation

Tosatti, Paolo, et al. "Catalyst Control in Sequential Asymmetric Allylic Substitution: Stereodivergent Access to N,N-diprotected Unnatural Amino Acids." The Journal of Organic Chemistry, vol. 76, no. 13, 2011, pp. 5495-501.
Tosatti P, Campbell AJ, House D, et al. Catalyst control in sequential asymmetric allylic substitution: stereodivergent access to N,N-diprotected unnatural amino acids. J Org Chem. 2011;76(13):5495-501.
Tosatti, P., Campbell, A. J., House, D., Nelson, A., & Marsden, S. P. (2011). Catalyst control in sequential asymmetric allylic substitution: stereodivergent access to N,N-diprotected unnatural amino acids. The Journal of Organic Chemistry, 76(13), 5495-501. https://doi.org/10.1021/jo200720c
Tosatti P, et al. Catalyst Control in Sequential Asymmetric Allylic Substitution: Stereodivergent Access to N,N-diprotected Unnatural Amino Acids. J Org Chem. 2011 Jul 1;76(13):5495-501. PubMed PMID: 21563816.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalyst control in sequential asymmetric allylic substitution: stereodivergent access to N,N-diprotected unnatural amino acids. AU - Tosatti,Paolo, AU - Campbell,Amanda J, AU - House,David, AU - Nelson,Adam, AU - Marsden,Stephen P, Y1 - 2011/06/08/ PY - 2011/5/14/entrez PY - 2011/5/14/pubmed PY - 2011/10/25/medline SP - 5495 EP - 501 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 13 N2 - The sequential use of Cu-catalyzed asymmetric allylic alkylation, olefin cross-metathesis, and Ir-catalyzed asymmetric allylic amination allows the concise, stereodivergent synthesis of complex chiral amines with complete regiocontrol and good diastereoselectivity, exemplified by the synthesis of a pair of diastereoisomeric unnatural branched amino acid derivatives. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21563816/Catalyst_control_in_sequential_asymmetric_allylic_substitution:_stereodivergent_access_to_NN_diprotected_unnatural_amino_acids_ L2 - https://doi.org/10.1021/jo200720c DB - PRIME DP - Unbound Medicine ER -