Regio- and diastereoselectivity in TiCl4-promoted reduction of 2-aryl-substituted cis-4-methyl-5-trifluoromethyl-1,3-dioxolanes
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Add time:07/29/2019 Source:sciencedirect.com
TiCl4-mediated reduction of both syn- and anti-(4S,5S)-2-aryl-4-methyl-5-trifluoromethyl-1,3-dioxolanes with Et3SiD furnished monodeuterated hydroxy ethers resulting from the same regio- and stereoselective CO bond cleavage (yields >80%; 82–92% de). Deuteride addition to the benzylidene acetal and removal of the alkyl moiety from the reaction product gave (R)-(α-2H)benzyl alcohol (90% ee), thus suggesting a new route to chiral 1-deuteriobenzyl alcohols. A mechanistic rationale is proposed and supported by theoretical calculations.
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