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Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations.
Org Biomol Chem. 2014 Mar 28; 12(12):1983-94.OB

Abstract

Intramolecular iridium-catalyzed allylic aminations of homochiral (E)-6-N-nosylaminohept-2-en-1-yl methyl carbonates were investigated. The relative position of the 2,5-substituents of the resulting pyrrolidines was found to be controlled by using both enantiomers (4 and 5) of the appropriate chiral ligand, demonstrating a simple and highly stereodivergent synthetic protocol. Selected trans- and cis-2,5-disubstituted 3-hydroxypyrrolidines (2a and 18a) were converted to (+)-bulgecinine (6) and (+)-preussin (7), respectively.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Natori Y
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan.
Kikuchi S
No affiliation info available
Kondo T
No affiliation info available
Saito Y
No affiliation info available
Yoshimura Y
No affiliation info available
Takahata H
No affiliation info available

MeSH

Allyl CompoundsAminationCatalysisIridiumMolecular ConformationPyrrolidinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24549243

Citation

Natori, Yoshihiro, et al. "Asymmetric Synthesis of 2,5-disubstituted 3-hydroxypyrrolidines Based On Stereodivergent Intramolecular Iridium-catalyzed Allylic Aminations." Organic & Biomolecular Chemistry, vol. 12, no. 12, 2014, pp. 1983-94.
Natori Y, Kikuchi S, Kondo T, et al. Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations. Org Biomol Chem. 2014;12(12):1983-94.
Natori, Y., Kikuchi, S., Kondo, T., Saito, Y., Yoshimura, Y., & Takahata, H. (2014). Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations. Organic & Biomolecular Chemistry, 12(12), 1983-94. https://doi.org/10.1039/c3ob42229a
Natori Y, et al. Asymmetric Synthesis of 2,5-disubstituted 3-hydroxypyrrolidines Based On Stereodivergent Intramolecular Iridium-catalyzed Allylic Aminations. Org Biomol Chem. 2014 Mar 28;12(12):1983-94. PubMed PMID: 24549243.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations. AU - Natori,Yoshihiro, AU - Kikuchi,Shunsuke, AU - Kondo,Takahiro, AU - Saito,Yukako, AU - Yoshimura,Yuichi, AU - Takahata,Hiroki, Y1 - 2014/02/19/ PY - 2014/2/20/entrez PY - 2014/2/20/pubmed PY - 2014/10/14/medline SP - 1983 EP - 94 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 12 IS - 12 N2 - Intramolecular iridium-catalyzed allylic aminations of homochiral (E)-6-N-nosylaminohept-2-en-1-yl methyl carbonates were investigated. The relative position of the 2,5-substituents of the resulting pyrrolidines was found to be controlled by using both enantiomers (4 and 5) of the appropriate chiral ligand, demonstrating a simple and highly stereodivergent synthetic protocol. Selected trans- and cis-2,5-disubstituted 3-hydroxypyrrolidines (2a and 18a) were converted to (+)-bulgecinine (6) and (+)-preussin (7), respectively. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/24549243/Asymmetric_synthesis_of_25_disubstituted_3_hydroxypyrrolidines_based_on_stereodivergent_intramolecular_iridium_catalyzed_allylic_aminations_ DB - PRIME DP - Unbound Medicine ER -