{"data":{"id":"10.6084/m9.figshare.c.3141922.v2","type":"dois","attributes":{"doi":"10.6084/m9.figshare.c.3141922.v2","prefix":"10.6084","suffix":"m9.figshare.c.3141922.v2","identifiers":[],"alternateIdentifiers":[],"creators":[{"name":"Weidong Shang","affiliation":[],"nameIdentifiers":[]},{"name":"Fairhurst, Magnus E.","nameType":"Personal","givenName":"Magnus E.","familyName":"Fairhurst","affiliation":[],"nameIdentifiers":[]},{"name":"Sydnes, Leiv K.","nameType":"Personal","givenName":"Leiv K.","familyName":"Sydnes","affiliation":[],"nameIdentifiers":[]}],"titles":[{"title":"Preparation of silyl-protected γ-hydroxylated α,β-unsaturated acetylenic ketones and their reactions with some nucleophiles"}],"publisher":"Figshare","container":{},"publicationYear":2016,"subjects":[{"subject":"Biochemistry"},{"subject":"29999 Physical Sciences not elsewhere classified","subjectScheme":"FOR"},{"subject":"FOS: Physical sciences","schemeUri":"http://www.oecd.org/science/inno/38235147.pdf","subjectScheme":"Fields of Science and Technology (FOS)"},{"subject":"FOS: Physical sciences","subjectScheme":"Fields of Science and Technology (FOS)"},{"subject":"Molecular Biology"},{"subject":"Pharmacology"},{"subject":"39999 Chemical Sciences not elsewhere classified","subjectScheme":"FOR"},{"subject":"FOS: Chemical sciences","schemeUri":"http://www.oecd.org/science/inno/38235147.pdf","subjectScheme":"Fields of Science and Technology (FOS)"},{"subject":"FOS: Chemical sciences","subjectScheme":"Fields of Science and Technology (FOS)"},{"subject":"Infectious Diseases"},{"subject":"FOS: Health sciences","schemeUri":"http://www.oecd.org/science/inno/38235147.pdf","subjectScheme":"Fields of Science and Technology (FOS)"},{"subject":"FOS: Health sciences","subjectScheme":"Fields of Science and Technology (FOS)"},{"subject":"Plant Biology"},{"subject":"FOS: Biological sciences","schemeUri":"http://www.oecd.org/science/inno/38235147.pdf","subjectScheme":"Fields of Science and Technology (FOS)"},{"subject":"FOS: Biological sciences","subjectScheme":"Fields of Science and Technology (FOS)"},{"subject":"Computational Biology"}],"contributors":[],"dates":[{"date":"2016-05-21","dateType":"Created"},{"date":"2016-06-01","dateType":"Updated"},{"date":"2016","dateType":"Issued"}],"language":null,"types":{"ris":"GEN","bibtex":"misc","citeproc":"article","schemaOrg":"Collection","resourceType":"Collection","resourceTypeGeneral":"Collection"},"relatedIdentifiers":[{"relationType":"IsSupplementTo","relatedIdentifier":"10.1080/00397911.2016.1172236","relatedIdentifierType":"DOI"},{"relationType":"IsIdenticalTo","relatedIdentifier":"10.6084/m9.figshare.c.3141922","relatedIdentifierType":"DOI"}],"relatedItems":[],"sizes":[],"formats":[],"version":null,"rightsList":[{"rights":"CC-BY","rightsUri":"http://creativecommons.org/licenses/by/3.0/us"}],"descriptions":[{"description":"A number of 5-siloxylated 1,1-diethoxy-3-alkyn-2-ones were prepared from the corresponding ketals. The t-butyldiphenylsiloxy derivatives were stable, whereas the trimethylsilyl analogs were unstable. The former compounds were reacted with diethylamine, lithium dimethylcuprate, and 1,3-propanedithiol and gave Michael adducts in good to very good yields. The amine and cuprate gave the conjugated alkenones, the former in a stereospecific manner (\u003ci\u003eZ\u003c/i\u003e), the latter stereospecifically (\u003ci\u003eE\u003c/i\u003e) in one case but otherwise stereoselectively with an \u003ci\u003eE\u003c/i\u003e preponderance. With the dithiol bisaddition occurred, and the corresponding 1,3-dithiane was obtained in excellent yield. Attempts to make 1,3-dithianes from 1,3-propanedithiol and 1,1-diethoxy-4-diethylaminoalk-3-en-2-ones failed.","descriptionType":"Abstract"}],"geoLocations":[],"fundingReferences":[],"xml":"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