DOI: 10.1246/cl.1988.1541. Diastereofacial Control in the Reaction of (R)-α-(<i>p</i>-Tolylsulfinyl)acetophenones with Several Organometallics

Diastereofacial Control in the Reaction of (R)-α-(p-Tolylsulfinyl)acetophenones with Several Organometallics

10.1246/cl.1988.1541

Crossref journal-article

Oxford University Press (OUP)

Chemistry Letters (286)

Abstract

Abstract The diastereofacial controlled addition of organometallics to optically active β-ketosulfoxide was achieved to furnish both diastereomers of β-hydroxy sulfoxide depending on the selection of organometallic reagents. Trichloromethyltitanium added to (R)-α-(p-tolylsulfinyl)acetophenones to give (RsRc)-β-hydroxy sulfoxides, while (RsSc)-β-hydroxy sulfoxides were obtained by utilizing trimethylaluminum. The utility of the present reaction was demonstrated in the synthesis of both enantiomers of sydowic acid.

Bibliography

Fujisawa, T., Fujimura, A., & Ukaji, Y. (1988). Diastereofacial Control in the Reaction of (R)-Î±-(p-Tolylsulfinyl)acetophenones with Several Organometallics. Chemistry Letters, 17(9), 1541â1544.

Authors 3

Tamotsu Fujisawa (first)
Atsushi Fujimura (additional)
Yutaka Ukaji (additional)

References 20 Referenced 24

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{'key': '2024011911113167600_r2'}
10.5059/yukigoseikyokaishi.44.576
10.5059/yukigoseikyokaishi.45.472
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10.1016/S0040-4039(00)61904-4
10.1246/bcsj.61.1273
{'key': '2024011911113167600_r8'}
{'key': '2024011911113167600_r9'}
{'key': '2024011911113167600_r10'}
10.1021/jo00195a006
10.1016/S0040-4039(00)94945-1
10.1002/anie.198405561
10.1007/BF02540819
{'key': '2024011911113167600_r15'}
{'key': '2024011911113167600_r16'}
{'key': '2024011911113167600_r17'}
{'key': '2024011911113167600_r18'}
10.1002/cber.19811140243
10.1021/ja00791a084

Dates

Type	When
Created	19 years, 1 month ago (July 24, 2006, 10:40 p.m.)
Deposited	1 year, 7 months ago (Jan. 19, 2024, 6:11 a.m.)
Indexed	1 year, 7 months ago (Jan. 19, 2024, 7:03 p.m.)
Issued	37 years ago (Sept. 1, 1988)
Published	37 years ago (Sept. 1, 1988)
Published Online	19 years, 5 months ago (March 27, 2006)
Published Print	36 years, 11 months ago (Sept. 5, 1988)

Funders 0

None

BibTeX

@article{Fujisawa_1988, title={Diastereofacial Control in the Reaction of (R)-α-(p-Tolylsulfinyl)acetophenones with Several Organometallics}, volume={17}, ISSN={1348-0715}, url={http://dx.doi.org/10.1246/cl.1988.1541}, DOI={10.1246/cl.1988.1541}, number={9}, journal={Chemistry Letters}, publisher={Oxford University Press (OUP)}, author={Fujisawa, Tamotsu and Fujimura, Atsushi and Ukaji, Yutaka}, year={1988}, month=sep, pages={1541–1544} }

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