Enantioselective Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters: Methodology and Applications

被引:169
作者
Sonawane, Ravindra P. [1 ]
Jheengut, Vishal [1 ]
Rabalakos, Constantinos [1 ]
Larouche-Gauthier, Robin [1 ]
Scott, Helen K. [1 ]
Aggarwal, Varinder K. [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
基金
英国工程与自然科学研究理事会; 欧洲研究理事会;
关键词
borates; chirality; natural products; olefination; stereogenic centers; ALGA SPOROCHNUS-BOLLEANUS; MARINE ALGA; ASYMMETRIC-SYNTHESIS; FISH DETERRENT; ALLYLIC SUBSTITUTIONS; MIGRATORY APTITUDES; ANTAGONIST LY426965; SECONDARY ALCOHOLS; CARBON CENTERS; ALKYL-GROUPS;
D O I
10.1002/anie.201008067
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pin it down: A range of substrates that bear versatile functional groups with quaternary stereogenic centers have been prepared with very high enantioselectivity from tertiary boronic esters (see scheme; Cb=N,N-diisopropylcarbamoyl, pin=pinacolato). The preparation of allylboronic esters bearing contiguous quaternary and tertiary stereogenic centers, and applications to natural product synthesis are also reported. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.
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页码:3760 / 3763
页数:4
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