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Synlett 2016; 27(02): 267-271
DOI: 10.1055/s-0035-1560595
DOI: 10.1055/s-0035-1560595
letter
(S)-Pyrrolidine-Containing Chiral Manganese(III)–Salalen and –Salan Complexes as Catalysts for the Asymmetric Henry Reaction
Further Information
Publication History
Received: 29 September 2015
Accepted after revision: 24 October 2015
Publication Date:
01 December 2015 (online)
Abstract
Chiral Mn(III)–salalen and –salan complexes derived from (S)-proline have been used as catalysts for the asymmetric Henry (nitro-aldol) reaction. We have also used this methodology for a variety of substrates to afford nitroaldol products in 40–94% yields with 25–92% ee.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560595.
- Supporting Information
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- 28 General Procedure for the Catalytic Asymmetric Nitroaldol Reaction Catalyst 2 (5 mol%, 13 mg) was dissolved in 2-PrOH (2 mL), and the requisite aldehyde (0.5 mmol) and MeNO2 (10 mmol) were added. The mixture was stirred at r.t. for 10 min then cooled to –35 °C, and DIPEA (5 mol%, 4.2 μL) was added. The reaction mixture was allowed to stir for the specified time, then the solvent was removed on a rotary evaporator, and the nitroaldol product was purified by column chromatography on silica gel (hexane–EtOAc, 80:20). The ee was determined by HPLC using Chiralcel OD-H, AD-H, and IC columns. 2-Nitro-1-(4-nitrophenyl)ethanol (10)14i Yellow oil, 91% yield, 80% ee. HPLC conditions: Diacel Chiralcel OD-H, hexane–i-PrOH (80:20, v/v), flow rate 1.00 mL/min, column temp 25 °C, UV λ = 230 nm), t R (major) = 11.92, t R (minor) = 13.55, [α]D 25 –19.4 (c 0.90, CHCl3). 1H NMR (400 MHz, CDCl3): δ = 8.31–7.61 (m, 4 H), 5.61–5.58 (dd, 2 H, J = 5.0 Hz), 4.51–4.57 (m, 1 H), 2.31 (br s, 1 H) ppm. 13C NMR(100 MHz, CDCl3): δ = 148.03, 145.00, 126.91 (2 C), 124.14 (2 C), 80.57, 69.90 ppm.
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