Synthesis of sterically demanding α-amino-β-hydroxy acids via anti -selective aldol reactions

Synlett

Volumn 1995, Issue 9, 1995, Pages 945-946

  Kazmaier, Uli ^a   Grandel, Roland ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Aldol reaction; Chelated enolate; alkylated amino acids; hydroxy amino acids

Indexed keywords

EID: 0002253972     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-5119     Document Type: Article

References (28)

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27. General procedure is as follows: To a THF solution of LDA (2.5 mmol) the amino acid ester (1 mmol) is added at-78C under an argon atmosphere. A THF solution of the metal salt (1.2 or 2.5 mmol) is added subsequently. After being stirred for 10 minutes, a THF solution of an aldehyde (1.2 mmol) is added and the stirring is continued. After 30 minutes reaction time the mixture is diluted with ether and hydrolyzed with IN hydrochloric acid. The organic layer is washed with IN NaOH solution, dried and evaporated. The product is purified by flash chromatography.
28. Spectral data of aldol product 5: anti-5: 1/8 NMR (CDC13) 5 0.81 (3H, d, J= 6.8 Hz, i-Pr CH3), 1.00 (3H, d, J= 6.6 Hz, /-Pr CH3), 1.46 (9H, s, /-Bu), 1.58 (3H, s, CH3), 3.64 (1H, dd, J= 7.3 Hz, J = 11.4 Hz, H-3), 4.74 (1H, d, ./= 11, 4 Hz, OH), 5.09 (2H, s, CH2), 6.36 (1H, s, NH), and 7.31-7.39 (5H, m, Ph); 13C NMR (CDC13) 6 18.98 (CH3), 20.23, 22.40, (/-Pr CH3), 27.65 (/-Bu), 32.26 (C-4), 63.73 (C-2), 67.08 (CH2), 80.11 (C-3), 83.23 (/-Bu), 127.94, 128.03, 128.18, 128.48, 136.04 (each Ph), 156.75 (OCON), and 172.96 (COO/-Bu). syn-5: 1/8 NMR (CDC13) 6 0.91 (3H, d, J = 6.7 Hz, /-Pr CH3), 1.01 (3H, d, J= 6.9 Hz, /-Pr CH3), 1.46 (9H, s, /-Bu), 1.55 (3H, s, CH3), 1.87-1.97 (1H, m, H-2), 3.14 (1H, s, OH), 3.77 (1H, dd, J = 7.4, 3.3 Hz, H-3), 5.05 (1H, d, JAB = 12.3 Hz, CH2), 5.12 (1H, d, = 12.2 Hz, CH2), 5.60 (1H, s, NH), and 7.31-7.37 (5H, m, Ph); 13C NMR (CDC13) 8 16.27 (CH3), 20.65, 21.97 (/-Pr CH3), 27.82 (/-Bu), 29.28 (C-4), 63.57 (C-2), 66.73 (CH2), 78.41 (C-3), 82.80 (/-Bu), 128.09, 128.47, 128.65, 136.39 (each Ph), 155.74 (OCON), and 172.59 (COO/-Bu).