Chromium-catalyzed asymmetric synthesis of 1,3-diols

An efficient,chromium-catalyzed highly enantioselective preparation of protected 1,3-diols has been achieved.In the presence of a chiral chromium catalyst using the carbazole-based bisoxazoline as the chiral ligand,a variety of optically pure 1,3-diols were synthesized in 34%-87%yields with up to 98...

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Published inChinese chemical letters Vol. 28; no. 6; pp. 1182 - 1184
Main Authors Ji, Hong-Tao, Tian, Qing-Shan, Xiang, Jian-Nan, Zhang, Guo-Zhu
Format Journal Article
LanguageEnglish
Published NEW YORK Elsevier B.V 01.06.2017
Elsevier
Subjects
1,3-Diol
Allylation
Asymmetric
Bisoxazoline
Chemistry
Chemistry, Multidisciplinary
Chromium-catalyzed
Physical Sciences
Science & Technology
Chromium-catalyzed
Asymmetric
1,3-Diol
Bisoxazoline
Allylation
HALIDES
(+)-TEDANOLIDE
ENANTIOSELECTIVE SYNTHESIS
COMPLEXES
ALDEHYDES
ALLYLIC ALCOHOLS
CARBONYL ALLYLATION
COUPLING REACTION
SNCL2
CHLORIDE
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Summary:An efficient,chromium-catalyzed highly enantioselective preparation of protected 1,3-diols has been achieved.In the presence of a chiral chromium catalyst using the carbazole-based bisoxazoline as the chiral ligand,a variety of optically pure 1,3-diols were synthesized in 34%-87%yields with up to 98%ee.The benzyl as well as silyl ethers were suitable substitutions for the hydroxyl group.Meanwhile,aromatic,aliphatic and α,β-unsaturated aldehydes are well tolerated under the mild reaction conditions.
Bibliography:1,3-Diol Asymmetric Chromium-catalyzed Allylation Bisoxazoline
An efficient,chromium-catalyzed highly enantioselective preparation of protected 1,3-diols has been achieved.In the presence of a chiral chromium catalyst using the carbazole-based bisoxazoline as the chiral ligand,a variety of optically pure 1,3-diols were synthesized in 34%-87%yields with up to 98%ee.The benzyl as well as silyl ethers were suitable substitutions for the hydroxyl group.Meanwhile,aromatic,aliphatic and α,β-unsaturated aldehydes are well tolerated under the mild reaction conditions.
11-2710/O6
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2017.03.016