A Practical and Enantiospecific Synthesis of (−)-(R)- and (+)-(S)-Piperidin-3-ols

A Practical and Enantiospecific Synthesis of (−)-(R)- and (+)-(S)-Piperidin-3-ols

A highly enantiospecific, azide‐free synthesis of (−)‐(R)‐ and (+)‐(S)‐piperidin‐3‐ol in excellent yield was developed. The key step of the synthesis involves the enantiospecific ring openings of enantiomerically pure (R)‐ and (S)‐2‐(oxiran‐2‐ylmethyl)‐1H‐isoindole‐1,3(2H)‐diones with the diethyl ma...

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Veröffentlicht in:Helvetica chimica acta 2014-11, Vol.97 (11), p.1507-1515
Hauptverfasser: Suresh Babu, Meruva, Raghunadh, Akula, Ramulu, Konda, Dahanukar, Vilas H., Syam Kumar, Unniaran K., Kumar Dubey, P.
Format: Artikel
Sprache:eng
Schlagworte:
3-diones
Decarboxylation
Epoxide opening
Isoindole-1
Isoindole‐1,3‐diones
Piperidin-3-ols
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Beschreibung
Zusammenfassung:A highly enantiospecific, azide‐free synthesis of (−)‐(R)‐ and (+)‐(S)‐piperidin‐3‐ol in excellent yield was developed. The key step of the synthesis involves the enantiospecific ring openings of enantiomerically pure (R)‐ and (S)‐2‐(oxiran‐2‐ylmethyl)‐1H‐isoindole‐1,3(2H)‐diones with the diethyl malonate anion and subsequent decarboxylation.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201400008