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A Chiral Benzyl Group as a Chiral Auxiliary and Protecting Group for the Synthesis of Optically Active 1,2-Diols and (+)-Frontalin

Authors
Kim, Tae HyunKim, Young-KyoYang, ZunhuaJung, Jung WhaJeong, Lak ShinKim, Hee-Doo
Issue Date
23-Jan-2014
Publisher
GEORG THIEME VERLAG KG
Keywords
nucleophilic addition; diols; -benzyloxy ketones; (+)-frontalin; stereoselective synthesis
Citation
SYNLETT, v.25, no.2, pp 251 - 254
Pages
4
Journal Title
SYNLETT
Volume
25
Number
2
Start Page
251
End Page
254
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/11003
DOI
10.1055/s-0033-1340163
ISSN
0936-5214
1437-2096
Abstract
Chelation-controlled asymmetric nucleophilic addition of a Grignard reagent to chiral -benzyloxy ketones gives the corresponding alcohols with high diastereoselectivities (up to 96% de) by 1,4-asymmetric induction. A chiral benzyl group is used as a chiral auxiliary as well as a protecting group for the synthesis of optically active 1,2-diols and (+)-frontalin.
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