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Volumn 50, Issue 51, 2011, Pages 12249-12252

Asymmetric synthesis of chiral 1,3-diaminopropanols: Bisoxazolidine- catalyzed C-C bond formation with α-keto amides

Author keywords

keto amides; asymmetric catalysis; bisoxazolidines; C C bond formation; nitroaldol reaction

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; BISOXAZOLIDINES; C-C BOND FORMATION; DEPROTECTION; NITROALDOL; REDUCTION REACTION;

EID: 83755196073     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201105778     Document Type: Article
Times cited : (48)

References (67)
  • 39
    • 33748063010 scopus 로고    scopus 로고
    • For an example of asymmetric catalysis with an α-formyl amide, see:, During the completion of this manuscript, the asymmetric intramolecular arylation of α-keto amides was reported
    • For an example of asymmetric catalysis with an α-formyl amide, see:, D. A. Evans, Y. Aye, J. Am. Chem. Soc. 2006, 128, 11034. During the completion of this manuscript, the asymmetric intramolecular arylation of α-keto amides was reported
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 11034
    • Evans, D.A.1    Aye, Y.2
  • 41
    • 79961224085 scopus 로고    scopus 로고
    • Racemic nitroaldol products of keto amides have been obtained by using catalytic amounts of diethyl- or triethylamine
    • Angew. Chem. Int. Ed. 2011, 50, 7620. Racemic nitroaldol products of keto amides have been obtained by using catalytic amounts of diethyl- or triethylamine
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 7620
  • 44
    • 83755162339 scopus 로고    scopus 로고
    • Nitroaldol products are known to easily decompose and racemize under basic and acidic conditions or upon heating
    • Nitroaldol products are known to easily decompose and racemize under basic and acidic conditions or upon heating.
  • 45
    • 83755181330 scopus 로고    scopus 로고
    • For desymmetrization of 1,3-propanediols and 1,2,3-propanetriols
    • For desymmetrization of 1,3-propanediols and 1,2,3-propanetriols, see
  • 57
    • 83755171327 scopus 로고    scopus 로고
    • This ligand is commercially available at Strem (cat. no. 07-0488), US Patent, 11/737,371, 2007
    • This ligand is commercially available at Strem (cat. no. 07-0488), US Patent, 11/737,371, 2007.
  • 58
    • 83755162338 scopus 로고    scopus 로고
    • note
    • We found that in most cases double condensation to generate a bisoxazolidine structure does not occur with a wide range of amino alcohols and diketones. In contrast, only one carbonyl group reacts even under harsh conditions to give a monooxazolidine, or other by-products are formed.
  • 63
    • 83755181328 scopus 로고    scopus 로고
    • note
    • The absolute configuration of the nitroaldol products was confirmed by NMR analysis with a chiral solvating agent (see the Supporting Information).
  • 64
    • 83755171325 scopus 로고    scopus 로고
    • note
    • The nitroaldol reaction with N-propyl and N-benzyl 2-oxo-2- phenylacetamide gave the product in 92-95-% yield and 26-30-% ee.
  • 67
    • 83755181324 scopus 로고    scopus 로고
    • note
    • Formation of the tBoc derivative of 25 and HPLC analysis on a chiral stationary phase (Chiralpak AD) showed that the ee value was slightly reduced from 90-% to 86-% after the two reduction steps (see the Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.