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Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer

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Citation

Mulzer, J., Kattner, L., Strecker, A. R., Schröder, C., Buschmann, J., Lehmann, C. W., et al. (1991). Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer. Journal of the American Chemical Society, 113(11), 4218-4229. doi:10.1021/ja00011a025.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-C265-8
Abstract
The chromium(II)-mediated addition (''Hiyama reaction'') of the chiral
allylic bromides 13, 15, 19, 22, 24, and 27 to achiral and chiral
aldehydes proceeds with high Felkin-Anh selectivity with respect to the
stereocenter at C-gamma in the bromide (Table II). By double
stereodifferentiation experiments (Tables III/IV) it was shown that the
bromide is the stereodominating component in the addition. The
methodology was applied to the first synthesis of nephromopsinic acid
(-)-69, found in the lichen species nephromopsis stracheyi, and its
enantiomer.