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Juaristi, E.; Muñoz-Muñiz, O.; Melgar-Fernández, R., Science of Synthesis, (2006) 8, 1280.
A further example of sodium enolate alkylation controlled by a chiral auxiliary involves the use of sultams that are readily prepared from 10-camphorsulfonyl chloride.[68,69] Because both enantiomers of this acid chloride are commercially available, both enantiomers of the chiral sultam are equally accessible. Acyl derivatives such as 82 can be prepared by treatment of sultam 81 with an acyl chloride in the presence of a base (Scheme 33).
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M8 | M8 | Meeeee,e (%) ee 88 | eee (%) ee 88 | Meeeee,e (%) ee 88 | eee,e (%) ee 88 | Mee |
---|---|---|---|---|---|---|
Me | Me | 888 | 88.8 | 88 | 88.8 | [88] |
Me | MM8MM=MM8 | 88 | 88.8 | 88 | 88.8 | [88] |
Me | MM8MM8e-Me | e.e. | 88.8 | 88 | >88 | [88] |
Me | MM8MMeMeee | e.e. | 88.8 | 88 | >88 | [88] |
Me | MM8MMee | e.e. | 88 | 88 | >88 | [88] |
Me | (MM8)8eMe | 88 | 88 | 88 | >88 | [88] |
Me | Me | 88 | 88.8 | 88 | 88.8 | [88] |
MMe | Me | 88 | 88.8 | e.e. | e.e. | [88] |
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Meeeeeeeee Meeee 88; Meeeeee Meeeeeeee:[88]
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M eeeeeee ee eeeeee 88 (8.8 e, 88 eeee), Me8M (88 eM, 88 eeee), eee MM8Me8 (88 eM) ee 8°M eee eeeeeee eeee M8MM8MMMe (88 eeee) ee MM8Me8 (88 eM) eee eee eeeeeee eee eeeeeee eee 8 e. Meeeee eee eeeeeeeeeeeeeee (eeeeee/Me8M) eeee eee M-eeee eeeeee 88 ee eeee eeeee.
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References
[68] | Meeeeeee, M.; Meeeeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[69] | Meeeeeee, M.; Meeeeee, M.; Meeeeeeeeeeee, M., Meee. Meee. Meee, (8888) 88, 8888. |
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- 8.Meeeee-Meee, (8888) M 88e, 888.