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Volumn 124, Issue 44, 2002, Pages 12964-12965

Asymmetric catalytic Mannich reactions catalyzed by urea derivatives: Enantioselective synthesis of β-aryl-β-amino acids

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID; UREA DERIVATIVE;

EID: 0037032312     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028353g     Document Type: Article
Times cited : (571)

References (41)
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    • note
    • Other imine protecting groups examined under the same reaction conditions: N-Cbz benzaldimine, 26% ee; N-tosyl benzaldimine, 0% ee.
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    • note
    • The enantioselectivity of this reaction is relatively insensitive to dilution, stoichiometry, and rate of nucleophile addition. No change in enantioselectivity was observed with solvents of low polarity, while strongly polar aprotic solvents led to dramatically poorer ee's. Use of protic solvents resulted in rapid decomposition of the imine.
  • 33
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    • 9d
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    • While HMPA has traditionally been used as a cosolvent for tertbutyldimethylsilylation of lithium enolates, both DMPU or 1-methyl-2-pyrrolidinone (NMP) are effective alternatives.
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    • Full details of catalyst structure/enantioselectivity profiles for both the Mannich and the Strecker reactions will be reported in due course.
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    • note
    • Thiohydantoin formation proved problematic in the preparation of thiourea derivatives bearing secondary amides. Detailed experimental procedures are provided as Supporting Information.
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    • Aliphatic N-Boc imines have as yet not been investigated because no useful method currently exists for their synthesis.
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