A Practical and Enantiospecific Synthesis of (−)‐(R)‐ and (+)‐(S)‐Piperidin‐3‐ols. Issue 11 (18th November 2014)

• Record Type: Journal Article
• Authors: Suresh Babu, Meruva; Raghunadh, Akula; Ramulu, Konda; Dahanukar, Vilas H.; Syam Kumar, Unniaran K.; Kumar Dubey, P.
• Is Part Of: Helvetica chimica acta. Volume 97:Issue 11(2014:Nov.)
• Page Start: 1507
• Page End: 1515
• Publication Date: 2014-11-18
• Subjects: Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201400008
• Languages: English
• ISSNs: 0018-019X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A highly enantiospecific, azide‐free synthesis of (−)‐(<italic>R</italic>)‐ and (+)‐(<italic>S</italic>)‐piperidin‐3‐ol in excellent yield was developed. The key step of the synthesis involves the enantiospecific ring openings of enantiomerically pure (<italic>R</italic>)‐ and (<italic>S</italic>)‐2‐(oxiran‐2‐ylmethyl)‐1<italic>H</italic>‐isoindole‐1, 3(2<italic>H</italic>)‐diones with the diethyl malonate anion and subsequent decarboxylation.</p> </abstract>