Remote acyclic diastereocontol involving a bicyclic metal chelate. High 1,5 asymmetric induction in the hydride reduction of δ-hydroxy ketones
✍ Scribed by Han-Cheng Zhang; Michael J. Costanzo; Bruce E. Maryanoff
- Book ID
- 104214495
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 393 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Swnmmy: A variety of educing agents was explored to &act stereoselective nduction of acyclic Shydroxy ketone 3a; R-Alpine-Hydride pmvided high aM sterwaelectivity (unci:syn = 7: 1). Reduction of 3b in cl-&cl2 with R-Alpine-Hydri& or Zn(BH& affo&d impressive anti smleetivity: 1O:l and 13:1, respectively. The swrxxhemical outcome is attributed to a bicyclic metal-chelatc species (viz, 10). Stereochemical mntml in nactions of acyclic molecules has attmcted a great &al of attention. Enormous advances have been made in the genen@n of new proximal (12 and 1,3) stemqeuic centers with a high level