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Chiral Acylsilanes in Organic Synthesis. Part 2 . The role of the solvent, the organometallic reagent, and the nature of the substrate for the diastereoselectivity of 1,2‐additions to racemic alkoxymethyl‐substituted acylsilanes
Author(s) -
Chapeaurouge Alexander,
Bienz Stefan
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760507
Subject(s) - chemistry , reagent , stereoselectivity , chelation , substrate (aquarium) , solvent , lewis acids and bases , group 2 organometallic chemistry , organic chemistry , medicinal chemistry , catalysis , molecule , oceanography , geology
The role of the solvent, the organometallic reagent, and the nature of the substrate for the diastereoselectivity of 1,2‐additions to racemic alkoxymethyl‐substituted acylsilanes was investigated with the acylsilanes 1a–d by variation of the reaction parameters. The results obtained in this study support strongly the previously proposed preferred ‘chelate‐controlled’ reaction path followed under several reaction conditions: highest stereoselectivities were obtained with the best chelating substrates reacting with the most Lewis ‐acidic organometallic reagents in the least donating solvents. It is shown that almost complete stereoselectivity can be obtained using optimal reaction conditions.