Synlett 2017; 28(11): 1295-1299
DOI: 10.1055/s-0036-1588141
cluster
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of anti-β-Hydroxy-α-amino Esters via an Organocatalyzed Decarboxylative Aldol Reaction

Taryn March
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, 606-8501 Kyoto, Japan   Email: takemoto@pharm.kyoto-u.ac.jp
,
Akihiro Murata
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, 606-8501 Kyoto, Japan   Email: takemoto@pharm.kyoto-u.ac.jp
,
Yusuke Kobayashi
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, 606-8501 Kyoto, Japan   Email: takemoto@pharm.kyoto-u.ac.jp
,
Yoshiji Takemoto*
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, 606-8501 Kyoto, Japan   Email: takemoto@pharm.kyoto-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 13 December 2016

Accepted: 09 January 2017

Publication Date:
03 February 2017 (online)

Abstract

The first enantioselective decarboxylative aldol addition with α-amido-substituted malonic acid half oxyesters (MAHOs) is described. The combined use of a newly designed bifunctional sulfonamide catalyst with pentafluorobenzoic acid as an additive afforded the β-hydroxy-α-amino acid derivatives in moderate to high yields and with high enantioselectivities.

Supporting Information

 
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  • 13 Representative Procedure for the Enantioselective Decarboxylative Aldol Reaction To a stirred solution of 1h (0.05 mmol) in dry CPME (0.5–1.0 mL) at 10–15 °C, was added o-nitrobenzaldehyde (37.8 mg, 0.25 mmol), catalyst 11 (5.2 mg, 20 mol%), and pentafluorobenzoic acid (2.1 mg, 20 mol%). The mixture was stirred at the same temperature for 48 h, before being directly purified by silica gel column chromatography (hexane–EtOAc) to give the anti -β-hydroxy-α-amino acid 13a. Phenyl (2S,3S)-2-[(9H-Fluoren-9-yl)methoxycarbonyl] amino-3-hydroxy-3-(2-nitrophenyl)propanoate (13a) 1H NMR (400 MHz, CDCl3): δ = 8.03 (d, J = 6.4 Hz, 1 H), 7.91–7.90 (m, 1 H), 7.75 (d, J = 6.4 Hz, 2 H), 7.66 (t, J = 6.2 Hz, 1 H), 7.55–7.47 (m, 3 H), 7.40–7.34 (m, 5 H), 7.30–7.21 (m, 3 H), 7.00 (d, J = 6.0 Hz, 2 H), 5.85–5.80 (m, 2 H), 5.02–4.99 (m, 1 H), 4.24–4.34 (m, 2 H), 4.19–4.15 (m, 1 H), 3.69 (bs, 1 H). 13C NMR (100 MHz, CDCl3): δ = 168.9, 156.1, 150.0, 147.8, 143.5, 141.2, 135.2, 133.7, 129.5, 129.4, 129.1, 127.7, 127.1, 126.2, 125.0, 124.8, 121.1, 119.9, 70.4, 67.4, 59.4, 46.9. IR (ATR): 3401, 1763, 1703, 1522 cm–1. ESI-HRMS: m/z calcd for C30H24N2NaO7 [M + Na]+: 547.1476; found: 547.1464. HPLC [Chiralpak AD, hexane–2-PrOH = 80:20, 0.8 mL/min, λ = 254 nm]: t R (major) = 34.1 min; t R (minor) = 24.7 min.