A straightforward approach towards substituted morita-baylis-hillman products via hydrostannation of acetylenic ketones

Synlett

Volumn , Issue 3, 2010, Pages 407-410

  Lakshmi, B Vasantha ^a   Kazmaier, Uli ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Aldol addition; Alkynes; Enolates; Hydrostannation; Molybdenum; Morita Baylis Hillman

Indexed keywords

ACETYLENE DERIVATIVE; ALDEHYDE DERIVATIVE; ALLENE DERIVATIVE; KETONE DERIVATIVE; MOLYBDENUM; TIN DERIVATIVE;

ALDOL REACTION; ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; HYDROSTANNATION; MORITA BAYLIS HILLMAN REACTION; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 76249104120     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219196     Document Type: Article

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60. General Procedure for One-Pot HydrostannationAldol Additions The acetylenic ketone (1.0 mmol), hydroquinone (10 ol%), and Mo(CO)3 (CNt-Bu)3 (MoBI3) (3 mol%) were dissolved in THF (3 mL) in a Schlenk tube under N2. Then Bu3SnH (1.2 mmol) and the corresponding aldehyde (1.2 mmol) were added, the flask was evacuated and flushed with CO. The mixture was warmed to 60 C for 6 h. After cooling to r.t., the solvent was removed in vacuo, and the reaction mixture was subjected to column chromatography (silica, EtOAchexanes).
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62. Analytical Data of Selected Products Aldol Product 4a 1H NMR (400 MHz, CDCl3): d = 7.73 (dd, J = 8.4, 1.6 Hz, 2H), 7.50 (tt, J = 7.6, 1.6 Hz, 1 H), 7.407.34 (m, 4 H), 7.32 7.26 (m, 2 H), 7.237.19 (m, 1 H), 5.91 (td, J = 7.6, 1.2 Hz, 1 H), 5.55 (s, 1 H), 3.24 (br s, 1 H, OH), 1.79 (q, J = 7.6 Hz, 2 H), 1.31 (sext, J = 7.6 Hz, 2 H), 0.75 (t, J = 7.6 Hz, 3 H) ppm. 13C NMR (100 MHz, CDCl3): d = 200.1, 141.5, 141.4, 137.7, 134.7, 133.3, 129.2, 128.4, 128.3, 127.6, 126.3, 76.5, 31.7, 22.2, 13.5 ppm. HRMS (CI): m/z calcd for C19H20O2 [M]+: 280.1463; found: 280.1461. Aldol Product (Z)-6a 1H NMR (400 MHz, CDCl3): d = 8.13 (d, J = 8.4 Hz, 2 H), 7.45 (d, J = 8.4 Hz, 2 H), 7.257.03 (m, 3 H), 7.06 (dd, J = 8.4, 1.6 Hz, 2 H), 5.92 (t, J = 7.6 Hz, 1 H), 5.42 (s, 1 H), 3.27 (br s, 1 H, OH), 2.902.70 (m, 4 H), 2.18 (q, J = 7.6 Hz, 2 H), 1.45 (sext, J = 7.6 Hz, 2 H), 0.91 (t, J = 7.6 Hz, 3 H) ppm. 13C NMR (100 MHz, CDCl3): d = 203.0, 150.6, 147.0, 146.9, 140.6, 140.5, 128.5, 128.3, 126.2, 126.0, 123.5, 69.8, 39.5, 30.8, 30.1, 22.0, 14.0 ppm. Aldol Product (E)-6a 1H NMR (400 MHz, CDCl3): d = 8.14 (d, J = 8.8 Hz, 2 H), 7.47 (d, J = 8.8 Hz, 2 H), 7.297.18 (m, 3 H), .11 (dd, J = 8.4, 1.6 Hz, 2 H), 6.87 (t, J = 7.6 Hz, 1 H), 5.69 (s, 1 H), 3.082.91 (m, 2 H), 2.85 (t, J = 7.6 Hz, 2 H), 2.43 (sext, J = 7.6 Hz, 1 H), 2.34 (sext, J = 7.6 Hz, 1 H), 1.56 (sext d, J = 7.6, 2.0 Hz, 2 H), 1.00 (t, J = 7.6 Hz, 3 H) ppm. 13C NMR (100 MHz, CDCl3): d = 203.0, 150.6, 147.0, 146.9, 140.6, 140.5, 128.5, 128.3, 126.3, 126.0, 123.5, 69.9, 39.5, 30.8, 30.1, 22.0, 14.0 ppm. HRMS (CI): m/z calcd for C21H23NO4 [M]+: 353.1627; found: 353.1647.