Octanol-Accelerated Baylis-Hillman Reaction

Kwang-Su Park; Jinyoung Kim; Hyunah Choo; Youhoon Chong

doi:10.1055/s-2007-968032

LETTER

Octanol-Accelerated Baylis-Hillman Reaction

Kwang-Su Park^a, Jinyoung Kim^a, Hyunah Choo*^b, Youhoon Chong*^a
^a Department of Bioscience and Biotechnology, Institute of Biomedical Science and Technology, Konkuk University, 1 Hwayang-dong, Gwangjin-gu, Seoul 143-701, Korea
Fax: +82(2)4548217; e-Mail: chongy@konkuk.ac.kr;
^b Life Sciences Division, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea
e-Mail: hchoo@kist.re.kr;

Abstract

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Abstract

The Baylis-Hillman reaction was greatly accelerated by use of octanol as an additive. Under the octanol-accelerated Baylis-Hillman conditions, unactivated aldehydes such as aliphatic aldehydes and aromatic aldehydes with electron-withdrawing substituents were readily converted into the desired products in good to high yields.

Key words

Baylis-Hillman reaction - octanol - additive - rate acceleration - aliphatic aldehydes

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References and Notes

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Spectroscopic Data for Compound 4.
IR (neat): 3415, 1665, 1635, 1088 cm^-1. ¹H NMR (400 MHz, CDCl₃): δ = 1.32 (d, J = 6.5 Hz, 3 H), 2.36 (s, 3 H), 3.31 (br s, 1 H), 4.66 (br s, 1 H), 6.08 (s, 1 H), 6.11 (s, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 200.19, 151.09, 124.27, 65.89, 25.90, 21.76. HRMS (ESI): m/z calcd for C₆H₁₀O₂ [M + H]: 114.0681; found: 114.0685.
Spectroscopic Data for Compound 6.
¹H NMR (400 MHz, CDCl₃): δ = 6.04 (s, 1 H), 5.85 (s, 1 H), 2.61-2.57 (m, 1 H), 2.55-2.50 (m, 1 H), 2.34 (s, 3 H), 2.13 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 207.59, 199.24, 147.52, 126.01, 42.20, 29.47, 25.61, 25.05.

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