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Stereoselective formation of trisubstituted (Z)-chloroalkenes adjacent to a tertiary carbon stereogenic center by organocuprate-mediated reduction/alkylation.
Org Lett. 2012 Sep 07; 14(17):4490-3.OL

Abstract

A robust and efficient method for the synthesis of trisubstituted (Z)-chloroalkenes is described. A one-pot reaction of γ,γ-dichloro-α,β-enoyl sultams involving organocuprate-mediated reduction/asymmetric alkylation affords α-chiral (Z)-chloroalkene derivatives in moderate to high yields with excellent diastereoselectivity, and allylic alkylation of internal allylic gem-dichlorides is also demonstrated. This study provides the first examples of the use of allylic gem-dichlorides adjacent to the chiral center for novel 1,4-asymmetric induction.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Narumi T
Department of Medicinal Chemistry, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kandasurugadai, Tokyo 101-0062, Japan.
Kobayakawa T
No affiliation info available
Aikawa H
No affiliation info available
Seike S
No affiliation info available
Tamamura H
No affiliation info available

MeSH

AlkenesAllyl CompoundsCarbonCatalysisHydrocarbons, ChlorinatedMolecular StructureOxidation-ReductionStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22900591

Citation

Narumi, Tetsuo, et al. "Stereoselective Formation of Trisubstituted (Z)-chloroalkenes Adjacent to a Tertiary Carbon Stereogenic Center By Organocuprate-mediated Reduction/alkylation." Organic Letters, vol. 14, no. 17, 2012, pp. 4490-3.
Narumi T, Kobayakawa T, Aikawa H, et al. Stereoselective formation of trisubstituted (Z)-chloroalkenes adjacent to a tertiary carbon stereogenic center by organocuprate-mediated reduction/alkylation. Org Lett. 2012;14(17):4490-3.
Narumi, T., Kobayakawa, T., Aikawa, H., Seike, S., & Tamamura, H. (2012). Stereoselective formation of trisubstituted (Z)-chloroalkenes adjacent to a tertiary carbon stereogenic center by organocuprate-mediated reduction/alkylation. Organic Letters, 14(17), 4490-3. https://doi.org/10.1021/ol301988d
Narumi T, et al. Stereoselective Formation of Trisubstituted (Z)-chloroalkenes Adjacent to a Tertiary Carbon Stereogenic Center By Organocuprate-mediated Reduction/alkylation. Org Lett. 2012 Sep 7;14(17):4490-3. PubMed PMID: 22900591.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective formation of trisubstituted (Z)-chloroalkenes adjacent to a tertiary carbon stereogenic center by organocuprate-mediated reduction/alkylation. AU - Narumi,Tetsuo, AU - Kobayakawa,Takuya, AU - Aikawa,Haruo, AU - Seike,Shunsuke, AU - Tamamura,Hirokazu, Y1 - 2012/08/17/ PY - 2012/8/21/entrez PY - 2012/8/21/pubmed PY - 2013/4/6/medline SP - 4490 EP - 3 JF - Organic letters JO - Org Lett VL - 14 IS - 17 N2 - A robust and efficient method for the synthesis of trisubstituted (Z)-chloroalkenes is described. A one-pot reaction of γ,γ-dichloro-α,β-enoyl sultams involving organocuprate-mediated reduction/asymmetric alkylation affords α-chiral (Z)-chloroalkene derivatives in moderate to high yields with excellent diastereoselectivity, and allylic alkylation of internal allylic gem-dichlorides is also demonstrated. This study provides the first examples of the use of allylic gem-dichlorides adjacent to the chiral center for novel 1,4-asymmetric induction. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/22900591/Stereoselective_formation_of_trisubstituted__Z__chloroalkenes_adjacent_to_a_tertiary_carbon_stereogenic_center_by_organocuprate_mediated_reduction/alkylation_ DB - PRIME DP - Unbound Medicine ER -