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Synfacts 2011(6): 0685-0685
DOI: 10.1055/s-0030-1260385
DOI: 10.1055/s-0030-1260385
Polymer-Supported Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Crotylation and Homopropargylation by Flow Technology
C. F. Carter, H. Lange, D. Sakai, I. R. Baxendale, S. V. Ley*
University of Cambridge, UK and Mitsubishi Tanabe Pharma Corporation, Yokohama, Japan
Further Information
Publication History
Publication Date:
19 May 2011 (online)
Significance
A new flow reaction technology for diastereoselective Roush crotylation and Marshall homopropargylation as well as in-line purification protocols was described. Thus, the flow Roush reaction of aldehydes 1 with boronate 2 gave the corresponding homoallyl alcohols 3 in 70-94% yield with syn selectivity (syn/anti = 3.6-20:1). Similarly, the diastereoselective flow Marshall homopropargylation of allene (P)-4 with aldehyde (S)-5 was carried out with BF3˙OEt2 to give homopropargyl alcohol 6 in 75% yield.