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Journal article

Novel ortho-alkoxy-substituted phosphorus ylides and their stereoselectivity in Wittig reactions

The stereochem. of the reactions between tris(2-methoxymethoxyphenyl)phosphonioethanide, -butanide (I) and -phenylmethanide and a variety of aldehydes was investigated. Ylides having a b-unbranched aliph. sidechain, such as I, and satd. straight-chain aldehydes give olefins with unprecedented cis-selectivity (cis/trans   200:1). [on SciFinder (R)]

    Keywords: Stereochemistry (of Wittig reactions of alkoxy-substituted phenylphosphorus ylides with aldehydes); Ylides Role: RCT (Reactant) ; RACT (Reactant or reagent) (phosphorus ; alkoxyphenyl- ; Wittig reactions of ; stereochem. of); Wittig reaction (stereoselectiv ; stereoselective Wittig alkoxyphenylphosphorus ylide; cis selectivity Wittig alkoxyphenylphosphorus ylide; methoxymethoxyphenylphosphonium prepn deprotonation Wittig

    Note:

    CAN 113:59299

    29-7

    Organometallic and Organometalloidal Compounds

    Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.

    Journal

    0039-7881

    written in English.

    66-25-1 (Hexanal); 100-52-7 (Benzaldehyde); 6728-26-3; 27593-24-4 (2-Hexynal) Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with alkoxy-substituted phenylphosphorus ylides, stereochem. of); 1754-88-7; 3728-50-5; 106445-87-8; 106445-88-9; 106445-89-0; 106445-90-3; 106445-91-4; 106445-93-6; 106445-94-7 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reactions of, with aldehydes, stereochem. of); 123-72-8 (Butanal); 123-73-9; 630-19-3; 2043-61-0 (Formylcyclohexane) Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reactions of, with phosphorus ylides, stereochem. of); 107-30-2 Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with phenol); 873-66-5P; 13389-42-9P; 16002-93-0P; 60919-80-4P; 106445-96-9P Role: FORM (Formation, nonpreparative), PREP (Preparation) (formation of, in stereoselective Wittig reaction); 690-08-4P; 128375-60-0P Role: FORM (Formation, nonpreparative), PREP (Preparation) (formation of, in stereoselective Wittig reactions); 16721-45-2P; 128399-07-5P; 128399-08-6P; 128399-09-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Wittig reactions of, with aldehydes, stereochem. of); 824-91-9P (Methoxymethyl phenyl ether) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and arylation by, of tri-Ph phosphite); 103-30-0P; 645-49-8P; 3909-96-4P; 39491-55-9P; 128375-58-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 82797-12-4P; 94372-07-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via stereoselective Wittig reaction); 762-63-0P; 766-90-5P; 7642-04-8P; 7642-15-1P; 7642-18-4P; 19398-88-0P; 37490-34-9P; 74392-43-1P; 74392-44-2P; 106445-95-8P; 128375-59-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via stereoselective Wittig reactions); 128375-56-4P; 128375-57-5P; 128399-10-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn., deprotonation, and subsequent Wittig reactions of, with aldehydes); 124629-80-7P (Tris(2-methoxymethoxyphenyl)phosphine) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn., deprotonation, and subsequent Wittig reactions of, with aldehydes, stereochem. of)

    Reference

    • LSCO-ARTICLE-1990-018

    Record created on 2006-03-03, modified on 2016-08-08

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