Asymmetric synthesis of tetrasubstituted cyclic amines via aza-Henry reaction using cinchona alkaloid sulfonamide/zinc(ii) catalysts

The first enantioselective aza-Henry reaction of non-activated cyclic iminoesters, derived from cyclic amino acids, has been developed. Good yields and enantioselectivities were observed for the reaction using our original cinchona alkaloid sulfonamide/zinc(ii) catalyst. The transition state was pro...

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Published inChemical communications (Cambridge, England) Vol. 58; no. 9; pp. 1318 - 1321
Main Authors Yasukawa, Naoki, Yamanoue, Ami, Takehara, Tsunayoshi, Suzuki, Takeyuki, Nakamura, Shuichi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 27.01.2022
Royal Society of Chemistry
Subjects
Alkaloids
Amines
Amino acids
Catalysts
Chemistry
Chemistry, Multidisciplinary
Enantiomers
Physical Sciences
Science & Technology
Stereoselectivity
Sulfonamides
Zinc
KETONES
2H-AZIRINES
ALKYLATION
N-BOC KETIMINES
ENANTIOSELECTIVE ADDITION
PHASE-TRANSFER CATALYSTS
EFFICIENT
ACID HALF THIOESTERS
NITROMETHANE
NITRO-MANNICH REACTION
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Summary:The first enantioselective aza-Henry reaction of non-activated cyclic iminoesters, derived from cyclic amino acids, has been developed. Good yields and enantioselectivities were observed for the reaction using our original cinchona alkaloid sulfonamide/zinc(ii) catalyst. The transition state was proposed to explain the stereoselectivity based on experiments and DFT calculations.
Bibliography:ObjectType-Article-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc06492d