Stereoselective synthesis of (Z)-11- and (E)-11-eicosenyl acetate.
نویسندگان
چکیده
منابع مشابه
Stereoselective synthesis of Z-alkenes.
This chapter offers a general review of the evolvement of methods for the stereoselective synthesis of Z-alkenes, with a focus on the development of catalytic systems towards this goal in recent years.
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11-Chloro-3-methoxy-2-undecenal was synthesized from 8-bromooctanol, and an annelation reaction with this aldehyde and ethyl acetoacetate proceeded to give the ethyl 6-(8-chlorooctyl)salicylate. Ethyl 6-(8-chlorooctyl)salicylate was converted to ethyl 6-(7-formylheptyl)-2-methoxybenzoate through the iodide after protection of the phenolic hydroxyl group. Finally, the Wittig reaction with the al...
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Bench-top-storable (Z)-enethiol reagents: gold (Z)-1-decenylthiolates were synthesized stereoselectively in high yields. They are stable upon storage at room temperature without protection from light, and react smoothly with various alkyl halides, α,β-unsaturated ketones, and electron-deficient aryl halides with excellent stereoselectivity.
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The first examples of catalyst-controlled stereoselective macrocyclic ring-closing metathesis reactions that generate Z-enoates as well as (E,Z)- or (Z,E)-dienoates are disclosed. Reactions promoted by 3.0-10 mol % of a Mo-based monoaryloxide pyrrolide complex proceed to completion within 2-6 h at room temperature. The desired macrocycles are formed in 79:21 to >98:2 Z/E selectivity; stereoisom...
متن کاملStereoselective Acetate Aldol Reactions
The stereochemical control of aldol reactions from unsubstituted enolor enolatelike species, what are known as acetate aldol reactions, has been a matter of concern for nearly 30 years [1, 2]. Indeed, pioneering studies soon recognized that the asymmetric installation of a single stereocenter in such aldol reactions was much more demanding than the simultaneous construction of two new stereocen...
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ژورنال
عنوان ژورنال: Agricultural and Biological Chemistry
سال: 1978
ISSN: 0002-1369,1881-1280
DOI: 10.1271/bbb1961.42.1973