ISSN:
0009-2940
Keywords:
Kew Words: Asymmetric induction / Alcohols, homoallylic, diastereoselective synthesis of / γ-Amino alcohols, diastereoselective synthesis of / Hydrogen bonding / [2,3] Sigmatropic rearrangement / Wittig rearrangement
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The stereochemistry of Wittig-Still rearrangements under the influence of an allylic stereogenic center attached to Bn2N or RNBoc groups is studied. Rearrangements are subject to stereocontrol through asymmetric induction. Stannylated allyl ethers 13 with Z double bonds give syn-configuration amino alcohols 15 exclusively (ds 〉95 : 〈 5 - 〉 99.8 : 〈 0.2). Stannanes of E configuration 14 lead to 15 less selectively (syn :anti = 46 : 54 - 92 : 8). X-ray structural data are provided for amino alcohol syn-15b and for the bis(carbamate) 17.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230323
