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Ir-catalyzed allylic amination/ring-closing metathesis: a new route to enantioselective synthesis of cyclic beta-amino alcohol derivatives.
J Org Chem. 2007 Sep 14; 72(19):7443-6.JO

Abstract

Ir-catalyzed allylic aminations of (E)-4-benzyloxy-2-butenyl methyl carbonate with benzylamine using Feringa's (Sa,Sc,Sc)-phosphoramidite as a chiral ligand afforded linear-aminated achiral product N,O-dibenzyl-4-amino-2-buten-1-ol regioselectively (linear/branched = >99/1), whereas the (E)-5-benzyloxy-2-pentenyl methyl carbonate showed completely opposite regioselectivity (linear/branched = >1/99) and afforded the optically active (3R)-N,O-dibenzylated 3-amino-1-penten-5-ol with very high enantioselectivity (96% ee), which was used as a key intermediate for the effective synthesis of various cyclic beta-amino alcohol derivatives through ring-closing metathesis in high yields.

Authors+Show Affiliations

Lee JH
Division of Nano Science (BK21)/Department of Chemistry, Ewha Womans University, 11-1 Daehyun-Dong, Seodaemun-Gu, 120-750 Seoul, Korea.
Shin S
No affiliation info available
Kang J
No affiliation info available
Lee SG
No affiliation info available

MeSH

Allyl CompoundsAminationAmino AlcoholsCatalysisCyclizationIridiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

17705538

Citation

Lee, Jun Hee, et al. "Ir-catalyzed Allylic Amination/ring-closing Metathesis: a New Route to Enantioselective Synthesis of Cyclic Beta-amino Alcohol Derivatives." The Journal of Organic Chemistry, vol. 72, no. 19, 2007, pp. 7443-6.
Lee JH, Shin S, Kang J, et al. Ir-catalyzed allylic amination/ring-closing metathesis: a new route to enantioselective synthesis of cyclic beta-amino alcohol derivatives. J Org Chem. 2007;72(19):7443-6.
Lee, J. H., Shin, S., Kang, J., & Lee, S. G. (2007). Ir-catalyzed allylic amination/ring-closing metathesis: a new route to enantioselective synthesis of cyclic beta-amino alcohol derivatives. The Journal of Organic Chemistry, 72(19), 7443-6.
Lee JH, et al. Ir-catalyzed Allylic Amination/ring-closing Metathesis: a New Route to Enantioselective Synthesis of Cyclic Beta-amino Alcohol Derivatives. J Org Chem. 2007 Sep 14;72(19):7443-6. PubMed PMID: 17705538.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ir-catalyzed allylic amination/ring-closing metathesis: a new route to enantioselective synthesis of cyclic beta-amino alcohol derivatives. AU - Lee,Jun Hee, AU - Shin,Seunghoon, AU - Kang,Jahyo, AU - Lee,Sang-gi, Y1 - 2007/08/18/ PY - 2007/8/21/pubmed PY - 2007/10/17/medline PY - 2007/8/21/entrez SP - 7443 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 72 IS - 19 N2 - Ir-catalyzed allylic aminations of (E)-4-benzyloxy-2-butenyl methyl carbonate with benzylamine using Feringa's (Sa,Sc,Sc)-phosphoramidite as a chiral ligand afforded linear-aminated achiral product N,O-dibenzyl-4-amino-2-buten-1-ol regioselectively (linear/branched = >99/1), whereas the (E)-5-benzyloxy-2-pentenyl methyl carbonate showed completely opposite regioselectivity (linear/branched = >1/99) and afforded the optically active (3R)-N,O-dibenzylated 3-amino-1-penten-5-ol with very high enantioselectivity (96% ee), which was used as a key intermediate for the effective synthesis of various cyclic beta-amino alcohol derivatives through ring-closing metathesis in high yields. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17705538/Ir_catalyzed_allylic_amination/ring_closing_metathesis:_a_new_route_to_enantioselective_synthesis_of_cyclic_beta_amino_alcohol_derivatives_ L2 - https://doi.org/10.1021/jo070998h DB - PRIME DP - Unbound Medicine ER -