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Synthesis of aryl group-modified DIOP dioxides (Ar-DIOPOs) and their application as modular Lewis base catalysts.
Org Biomol Chem. 2012 Jun 21; 10(23):4562-70.OB

Abstract

Treatment of an optically pure tartaric acid-derived diiodide and various secondary phosphine oxides with LHMDS provides the corresponding aryl group-modified DIOP dioxides (Ar-DIOPOs). The activities of Ar-DIOPOs as Lewis base catalysts were investigated for several asymmetric transformations using chlorosilane reagents. The p-tolyl-substituted DIOPO (p-tolyl-DIOPO) was most effective for the reductive aldol reaction of chalcone and aldehydes with trichlorosilane, whereas the 2,8-dimethylphenoxaphosphine-derived DIOPO (DMPP-DIOPO) afforded the best enantioselectivity for the phosphonylation of conjugated aldehydes and the chlorinative aldol reaction of an ynone and benzaldehyde.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Ohmaru Y
Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan.
Sato N
No affiliation info available
Mizutani M
No affiliation info available
Kotani S
No affiliation info available
Sugiura M
No affiliation info available
Nakajima M
No affiliation info available

MeSH

AldehydesButanesCatalysisLewis BasesMolecular StructureOxidation-ReductionOxidesPhosphinesStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

22569566

Citation

Ohmaru, Yusuke, et al. "Synthesis of Aryl Group-modified DIOP Dioxides (Ar-DIOPOs) and Their Application as Modular Lewis Base Catalysts." Organic & Biomolecular Chemistry, vol. 10, no. 23, 2012, pp. 4562-70.
Ohmaru Y, Sato N, Mizutani M, et al. Synthesis of aryl group-modified DIOP dioxides (Ar-DIOPOs) and their application as modular Lewis base catalysts. Org Biomol Chem. 2012;10(23):4562-70.
Ohmaru, Y., Sato, N., Mizutani, M., Kotani, S., Sugiura, M., & Nakajima, M. (2012). Synthesis of aryl group-modified DIOP dioxides (Ar-DIOPOs) and their application as modular Lewis base catalysts. Organic & Biomolecular Chemistry, 10(23), 4562-70. https://doi.org/10.1039/c2ob25338k
Ohmaru Y, et al. Synthesis of Aryl Group-modified DIOP Dioxides (Ar-DIOPOs) and Their Application as Modular Lewis Base Catalysts. Org Biomol Chem. 2012 Jun 21;10(23):4562-70. PubMed PMID: 22569566.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of aryl group-modified DIOP dioxides (Ar-DIOPOs) and their application as modular Lewis base catalysts. AU - Ohmaru,Yusuke, AU - Sato,Norimasa, AU - Mizutani,Makoto, AU - Kotani,Shunsuke, AU - Sugiura,Masaharu, AU - Nakajima,Makoto, Y1 - 2012/05/09/ PY - 2012/5/10/entrez PY - 2012/5/10/pubmed PY - 2012/9/22/medline SP - 4562 EP - 70 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 10 IS - 23 N2 - Treatment of an optically pure tartaric acid-derived diiodide and various secondary phosphine oxides with LHMDS provides the corresponding aryl group-modified DIOP dioxides (Ar-DIOPOs). The activities of Ar-DIOPOs as Lewis base catalysts were investigated for several asymmetric transformations using chlorosilane reagents. The p-tolyl-substituted DIOPO (p-tolyl-DIOPO) was most effective for the reductive aldol reaction of chalcone and aldehydes with trichlorosilane, whereas the 2,8-dimethylphenoxaphosphine-derived DIOPO (DMPP-DIOPO) afforded the best enantioselectivity for the phosphonylation of conjugated aldehydes and the chlorinative aldol reaction of an ynone and benzaldehyde. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/22569566/Synthesis_of_aryl_group_modified_DIOP_dioxides__Ar_DIOPOs__and_their_application_as_modular_Lewis_base_catalysts_ L2 - https://doi.org/10.1039/c2ob25338k DB - PRIME DP - Unbound Medicine ER -