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Asymmetric synthesis of methyl (2R,3S)-3-(4-methoxyphenyl) glycidate, a key intermediate of diltiazem, via Mukaiyama aldol reaction

✍ Scribed by Ritsuo Imashiro; Tooru Kuroda


Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
62 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis


OMe

OAc O NMe


πŸ“œ SIMILAR VOLUMES


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## Abstract The cyclopropanation of the bislactim ethers 3 with diiodomethanes and diethylzinc proceeds in good yields and with high diastereoselectivities, affording the cyclopropyl bislactim ethers 6. Protection of the hydroxy group and subsequenthydrolysis furnish virtually enantiomerically and

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## Abstract The titanium derivative 2 of the bislactim ether 1 of cyclo(‐L‐Val‐Gly‐) reacts with aldehydes and ketones 3 highly diastereoselectively to give the __syn__‐addition products 4. Upon hydrolysis with diluted trifluoroacetic acid the compounds 4 yield besides methyl L‐valinate the (2__R__

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The titanium derivative 4a of the bislactim ether l a from cyclo-(L-Val-Gly) reacts with + m a t u r a t e d aldehydes 5 exclusively by 1.2-addition in a highly diastereowlective mode to give virtually only the (2R,l'S) diastereomers of type 6. Upon hydrolysis these furnish the methyl (2R,3S)-thrm-2