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ChemInform Abstract: Diastereoselective Simmons—Smith Cyclopropanations of Allylic Amines and Carbamates.

✍ Scribed by Stephen G. Davies; Kenneth B. Ling; Paul M. Roberts; Angela J. Russell; James E. Thomson


Publisher
John Wiley and Sons
Year
2008
Weight
39 KB
Volume
39
Category
Article
ISSN
0931-7597

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Asymmetric Simmons-Smith Cyclopropanation of α,β-Unsaturated Bornane-2,3-diol Acetals. -Reaction of selected α,β-unsaturated aldehydes (II) with bornanediol (I) affords novel chiral acetals (III), which undergo diastereoselective cyclopropanation with a Simmons-Smith reagent giving compounds (V). -

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Hydroxyl-versus Amide-Directed Cyclopropanation from the Allylic Position in 1-Hydroxy-4-N-acyl-cyclopentenes under Modified Simmons-Smith Conditions. -It is clearly demonstrated that the Ac group of the title cyclopentenes (III) and (VI) exerts a stronger diastereofacial directing effect than the