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Stereoselective synthesis of alcohols, XXXVI. Stereoselective generation of homoallyl alcohols having quaternary stereogenic centers

✍ Scribed by Hoffmann, Reinhard W. ;Schlapbach, Achim

Book ID
102901354
Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
617 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

E‐ and Z‐γ,γ‐disubstituted allylboronates 12 have been generated by the carbocupration of alkynes and subsequent homologation. These allylboronates add to aldehydes, forming the homoallyl alcohols 13 and 14 with 88–99% simple diastereoselectivity. The highest diastereoselectivity was obtained with α‐branched aldehydes.

πŸ“œ SIMILAR VOLUMES

Stereoselective synthesis of alcohols, X
Stereoselective synthesis of alcohols, XLI. Chirality transfer to generate quaternary stereogenic centers by an allylboration reaction
✍ Hoffmann, Reinhard W. ;Schlapbach, Achim πŸ“‚ Article πŸ“… 1991 πŸ› John Wiley and Sons 🌐 English βš– 399 KB πŸ‘ 1 views

## Abstract The acyclic alcohols 13 and 14 having a neighboring quaternary stereogenic center can be obtained in diastereoselectivities of > 95% by addition of the ß,Ξ³,γ‐trisubstituted allylboronates 12 to aldehydes. Starting from the nonracemic allylboronates 19 of presumed 84–92% e.e., we have ob