Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 16, Pages 3002-3008Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800220
Keywords
Kinetic resolution; organosilicon; 1; 3-dipolar cycloaddition; chiral ligand; copper
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Funding
- National Natural Science Foundation of China [21472031, 21503060, 21702211, 21773051]
- Zhejiang Provincial Natural Science Foundation of China [LZ18B020001, LY16E030009, LY17E030003, LY17B030005]
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The development of new strategies or reaction processes that tease new reactivity of functional groups continues to spur synthetic chemists toward innovative solutions that access new compounds. Herein, we find that the silicon-based bulky group enables a 1,3-dipolar addition-initiated parallel kinetic resolution (PKR) to occur unexpectedly, leading to the highly enantioselective synthesis of two structurally different types of amino acid derivatives via chemodivergent [3+2] cycloaddition reactions and tandem conjugate addition-elimination reaction respectively. The resulting and structurally divergent enantioenriched amino acid derivatives that contain four contiguous stereogenic centers and an all-carbon quaternary center were obtained with up to 99% ee with >95:1 dr and good yields.
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