ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Using readily accessible 10-sulfonamido-isoborneols as regenerable, chiral auxiliaries, highly face-selective C-C-bond formations at Cα and Cβ of carboxylates could be conveniently achieved. Thus, conjugated additions of RCu to enoates (1→2) furnished, after saponification, β-substituted carboxylic acids 3 in 94-98% e.e. Similarly, propionates 12 yielded after deprotonation, enolate alkylation, and reductive ester cleavage the (R)-alcohols 15 in 78-98% e.e. The acid (+)-3e was converted to the pheromone (-)-11.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680126
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