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Volumn 53, Issue 18, 2014, Pages 4642-4647

Stereocontrolled synthesis of syn-β-hydroxy-α-amino acids by direct aldolization of pseudoephenamine glycinamide

Author keywords

aldol reaction; amino acids; asymmetric synthesis; chiral auxiliaries; synthetic methods

Indexed keywords

ALDEHYDES; CONDENSATION REACTIONS; HYDROLYSIS; KETONES; LITHIUM; STEREOCHEMISTRY;

EID: 84899656982     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201400928     Document Type: Article
Times cited : (47)

References (105)
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    • For practical, scalable syntheses of (R,R)- and (S,S)-pseudoephenamine, see
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    • For the alkylation of pseudoephenamine amides, see
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    • For the synthesis and alkylation of pseudoephenamine alaninamide pivaldimine, see.
    • For the synthesis and alkylation of pseudoephenamine alaninamide pivaldimine, see:, C. L. Hugelshofer, K. T. Mellem, A. G. Myers, Org. Lett. 2013, 15, 3134-3137.
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    • We have previously proposed N→O-acyl transfer products as important intermediates in both acidic and alkaline hydrolyses of pseudoephedrine amides. See Ref. [3b] and the following paper.
    • We have previously proposed N→O-acyl transfer products as important intermediates in both acidic and alkaline hydrolyses of pseudoephedrine amides. See Ref. [3b] and the following paper:, A. G. Myers, B. H. Yang, H. Chen, L. McKinstry, D. J. Kopecky, J. L. Gleason, J. Am. Chem. Soc. 1997, 119, 6496-6511.
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    • Word Health Organization Model List of Essential Medicines, 18th edition: http://www.who.int/medicines/publications/essentialmedicines/en/ (Accessed December, 2013).
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    • The reduction of α-amino esters with sodium borohydride is well precedented. For an early, detailed study, see.
    • The reduction of α-amino esters with sodium borohydride is well precedented. For an early, detailed study, see:, H. Seki, K. Koga, H. Matsuo, S. Ohki, I. Matsuo, S. Yamada, Chem. Pharm. Bull. 1965, 13, 995-1000.
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    • For related methodology from the Evans group using α-halo enolates, see.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.