Imides, Mitsunobu reaction, alcohol-amine

Another approach to the preparation of iV-alkyl derivatives 26 is the Mitsunobu reaction. The Mitsunobu procedure is now a well-known method for preparing amines from alcohols using acidic imide derivatives as a nitrogen nucleophile < 198IS 1, 19960PP127>. The remarkably high acidity of l,2,4-dithiazolidine-3,5-dione 12 (pA), 2.8) <2000SL1622>... 

It has been found that the results of this new variant of the Mitsunobu procedure are generally comparable with the results of the traditional Mitsunobu reaction both with respect to the yields and enantiomeric excess (ee) of chiral compounds 26. Thus, products prepared from alcohol 86e using both methods had ee 70% and 72%, and from (Tl-methyl lactate 86i 92% and 99%, respectively. However the new variant of the Mitsunobu procedure has a significant synthetic advantage over the traditional procedure imides 26 can be transformed into primary amines under milder conditions in comparison with the deprotection of /V-alkylphthalimides (see Section 6.03.6.1.3). 

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