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BINAP/AgOTf/KF/18-crown-6 as new bifunctional catalysts for asymmetric Sakurai-Hosomi allylation and Mukaiyama aldol reaction.
J Org Chem. 2003 Jul 11; 68(14):5593-601.JO

Abstract

A catalytic amount of KF.18-crown-6 complex is effective as a soluble fluoride source to activate an asymmetric Sakurai-Hosomi allylation with BINAP and silver(I) triflate catalyst. The allylation of a variety of aromatic, alpha,beta-unsaturated and aliphatic aldehydes with allylic trimethoxysilane resulted in high yields and remarkable enantioselectivities. In addition, the asymmetric Mukaiyama-type aldol reaction is achieved by using trimethoxysilyl enol ethers in the presence of the same catalysts. High anti selectivity is obtained from E-silyl enol ether, while Z-silyl enol ether gives syn selectivity.

Authors+Show Affiliations

Graduate School of Engineering, Nagoya University, SORST, Japan Science and Technology Corporation (JST), Chikusa, Nagoya 464-8603, Japan.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

12839451

Citation

Wadamoto, Manabu, et al. "BINAP/AgOTf/KF/18-crown-6 as New Bifunctional Catalysts for Asymmetric Sakurai-Hosomi Allylation and Mukaiyama Aldol Reaction." The Journal of Organic Chemistry, vol. 68, no. 14, 2003, pp. 5593-601.
Wadamoto M, Ozasa N, Yanagisawa A, et al. BINAP/AgOTf/KF/18-crown-6 as new bifunctional catalysts for asymmetric Sakurai-Hosomi allylation and Mukaiyama aldol reaction. J Org Chem. 2003;68(14):5593-601.
Wadamoto, M., Ozasa, N., Yanagisawa, A., & Yamamoto, H. (2003). BINAP/AgOTf/KF/18-crown-6 as new bifunctional catalysts for asymmetric Sakurai-Hosomi allylation and Mukaiyama aldol reaction. The Journal of Organic Chemistry, 68(14), 5593-601.
Wadamoto M, et al. BINAP/AgOTf/KF/18-crown-6 as New Bifunctional Catalysts for Asymmetric Sakurai-Hosomi Allylation and Mukaiyama Aldol Reaction. J Org Chem. 2003 Jul 11;68(14):5593-601. PubMed PMID: 12839451.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - BINAP/AgOTf/KF/18-crown-6 as new bifunctional catalysts for asymmetric Sakurai-Hosomi allylation and Mukaiyama aldol reaction. AU - Wadamoto,Manabu, AU - Ozasa,Nobuko, AU - Yanagisawa,Akira, AU - Yamamoto,Hisashi, PY - 2003/7/4/pubmed PY - 2003/7/4/medline PY - 2003/7/4/entrez SP - 5593 EP - 601 JF - The Journal of organic chemistry JO - J Org Chem VL - 68 IS - 14 N2 - A catalytic amount of KF.18-crown-6 complex is effective as a soluble fluoride source to activate an asymmetric Sakurai-Hosomi allylation with BINAP and silver(I) triflate catalyst. The allylation of a variety of aromatic, alpha,beta-unsaturated and aliphatic aldehydes with allylic trimethoxysilane resulted in high yields and remarkable enantioselectivities. In addition, the asymmetric Mukaiyama-type aldol reaction is achieved by using trimethoxysilyl enol ethers in the presence of the same catalysts. High anti selectivity is obtained from E-silyl enol ether, while Z-silyl enol ether gives syn selectivity. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/12839451/BINAP/AgOTf/KF/18_crown_6_as_new_bifunctional_catalysts_for_asymmetric_Sakurai_Hosomi_allylation_and_Mukaiyama_aldol_reaction_ L2 - https://doi.org/10.1021/jo020691c DB - PRIME DP - Unbound Medicine ER -
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