Tetrahedron Letters p. 2919 - 2922 (1991)
Update date:2022-08-04
Topics:
Ukaji, Yutaka
Yamamoto, Kouji
Fukui, Masashi
Fujisawa, Tamotsu
It was observed that diastereoselectivity in an addition reaction to chiral 2-acyl oxazolidine, derived from (S)-prolinol, can be fully regulated under appropriate conditions. Addition of organotitanium triisopropoxides provided (S)-tertiary alcohols, while organolithium reagents afforded the corresponding (R)-alcohols. Application of this methodology was demonstrated in the synthesis of (+)- and (-)-trihexyphenidyl.
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