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A Stereoselective Access to Cyclic cis ‐1,2‐Amino Alcohols from trans ‐1,2‐Azido Alcohol Precursors
Author(s) -
Kim Donggil,
Jeong Wook,
Lee Won Jong,
Kang Soyeong,
Pak Han Kyu,
Park Jaiwook,
Rhee Young Ho
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500267
Subject(s) - chemistry , stereoselectivity , alcohol , ruthenium , alkoxy group , catalysis , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , alkyl
A unique one‐pot synthesis of cyclic cis ‐1,2‐amino alcohols from trans ‐1,2‐azido alcohol precursors was developed. The key step is highlighted by the stereoselective reduction of the cyclic α‐alkoxy imines, which could be prepared from the corresponding azides by ruthenium catalysis under photolytic conditions. Remarkably, this unprecedented reaction pathway offers a stereodivergent access to structurally diverse cyclic 1,2‐amino alcohols.