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Asymmetric Synthesis of (1,3‐Butadien‐2‐yl)methanols from Aldehydes via [1‐(Silylmethyl)allenyl]methanols
Author(s) -
DuránGalván María,
Connell Brian T.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000199
Subject(s) - chemistry , trimethylsilane , regioselectivity , carbazole , catalysis , organic chemistry , combinatorial chemistry , medicinal chemistry
Abstract [1‐(Silylmethyl)allenyl]methanols 2 were efficiently synthesized from aldehydes and (4‐bromobut‐2‐ynyl)trimethylsilane in the presence of a catalytic amount of CrCl 2 and tridentate carbazole ligands. The desired compounds were obtained with good yields (43–88 %) and enantioselectivities (55–78 % ee ). Alcohols 2 may be treated with TBAF or 2 M HCl in the case of aliphatic substrates, to provide (1,3‐butadien‐2‐yl)methanols 3 in 43–81 % yields. This method allows the synthesis of dienes 3 with no regioselectivity problems, and it tolerates a large number of functionalities.