ISSN:
0009-2940
Keywords:
Asymmetric induction / Alcohols, diastereoselective synthesis of / Alcohols, homoallylic / [2,3] wittig rearrangement
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Witting rearrangement of he type4→5 can exhibit stereocontrol due to asymmetric induction. The Wittig-still rearrangements of stannylated ethers (E)-10 and (Z)-10 are stereochemically complementary and furnish the homoallylic alcohols anti-11 and syn-11 with high diastereoselectivity (ds = 95:5 and 97:3, respectively. The 1,3-asymmetric induction established in the transformation of ether (Z)-10 can be reversed and combined with a 1,4-asymmetric induction as shown by the stereoselective Witting rearrangement of allyl propargyl ether 28 (ds = 88:6:5:1). 1,4-Asymmetric induction alone was observed neither in the [2,3] Wittig rearrangement tof propargyl ether 34 nor in that of (allyloxy)acetate 37.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230443
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