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Sakurai reaction of 3,3-bis(silyl) silyl enol ethers with acetals involving selective desilylation of the geminal bis(silane). Concise synthesis of nematocidal oxylipid.
Org Lett. 2013 Mar 01; 15(5):1068-71.OL

Abstract

3,3-Bis(silyl) silyl enol ethers have been shown to exhibit predominantly Sakurai reactivity, rather than Mukaiyama aldol reactivity, in their Lewis acid promoted reactions with acetals. Starting from a geminal bis(silyl) moiety consisting of two different silyl groups, such as SiMe(3) and SiMe(2)Ph, the SiMe(3) is selectively eliminated to give monoprotected E- vinylsilyl diols with good to excellent syn-diastereoselectivity. This reaction also underpinned a synthesis of the nematocidal oxylipid from Notheia anomala, demonstrating the attractive bifunctionality of geminal bis(silanes).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li L
Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China.
Ye X
No affiliation info available
Wu Y
No affiliation info available
Gao L
No affiliation info available
Song Z
No affiliation info available
Yin Z
No affiliation info available
Xu Y
No affiliation info available

MeSH

AcetalsAldehydesAntinematodal AgentsCombinatorial Chemistry TechniquesLewis AcidsMolecular StructureOxylipinsPhaeophytaSilanesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23398287

Citation

Li, Linjie, et al. "Sakurai Reaction of 3,3-bis(silyl) Silyl Enol Ethers With Acetals Involving Selective Desilylation of the Geminal Bis(silane). Concise Synthesis of Nematocidal Oxylipid." Organic Letters, vol. 15, no. 5, 2013, pp. 1068-71.
Li L, Ye X, Wu Y, et al. Sakurai reaction of 3,3-bis(silyl) silyl enol ethers with acetals involving selective desilylation of the geminal bis(silane). Concise synthesis of nematocidal oxylipid. Org Lett. 2013;15(5):1068-71.
Li, L., Ye, X., Wu, Y., Gao, L., Song, Z., Yin, Z., & Xu, Y. (2013). Sakurai reaction of 3,3-bis(silyl) silyl enol ethers with acetals involving selective desilylation of the geminal bis(silane). Concise synthesis of nematocidal oxylipid. Organic Letters, 15(5), 1068-71. https://doi.org/10.1021/ol400069p
Li L, et al. Sakurai Reaction of 3,3-bis(silyl) Silyl Enol Ethers With Acetals Involving Selective Desilylation of the Geminal Bis(silane). Concise Synthesis of Nematocidal Oxylipid. Org Lett. 2013 Mar 1;15(5):1068-71. PubMed PMID: 23398287.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Sakurai reaction of 3,3-bis(silyl) silyl enol ethers with acetals involving selective desilylation of the geminal bis(silane). Concise synthesis of nematocidal oxylipid. AU - Li,Linjie, AU - Ye,Xincui, AU - Wu,Ya, AU - Gao,Lu, AU - Song,Zhenlei, AU - Yin,Zhiping, AU - Xu,Yongjin, Y1 - 2013/02/11/ PY - 2013/2/13/entrez PY - 2013/2/13/pubmed PY - 2013/7/3/medline SP - 1068 EP - 71 JF - Organic letters JO - Org Lett VL - 15 IS - 5 N2 - 3,3-Bis(silyl) silyl enol ethers have been shown to exhibit predominantly Sakurai reactivity, rather than Mukaiyama aldol reactivity, in their Lewis acid promoted reactions with acetals. Starting from a geminal bis(silyl) moiety consisting of two different silyl groups, such as SiMe(3) and SiMe(2)Ph, the SiMe(3) is selectively eliminated to give monoprotected E- vinylsilyl diols with good to excellent syn-diastereoselectivity. This reaction also underpinned a synthesis of the nematocidal oxylipid from Notheia anomala, demonstrating the attractive bifunctionality of geminal bis(silanes). SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23398287/Sakurai_reaction_of_33_bis_silyl__silyl_enol_ethers_with_acetals_involving_selective_desilylation_of_the_geminal_bis_silane___Concise_synthesis_of_nematocidal_oxylipid_ L2 - https://doi.org/10.1021/ol400069p DB - PRIME DP - Unbound Medicine ER -