@article{b3af5532c27b47c4bbf6cb8067731ef6,
title = "Reductive routes to rigid peptide building blocks: The dependence of a regioselective imide reduction on the nature of an α-alkoxy substituent",
abstract = "The reduction of several N-acylpyrrolidinones has been studied. The regioselectivity of the reductions was found to depend on the nature of the N-acyl group. In one example, the use of a sterically bulky triisopropylsiloxy substituent alpha to the N-acyl carbonyl led to exclusive reduction of the pyrrolidinone carbonyl and the formation of a product that could be used in the synthesis of the 1-azabicyclo[5.3.0]decane ring skeleton found in a key bicyclic Pro-Phe building block.",
author = "Moeller, {Kevin D.} and Hanau, {Cathleen E.}",
note = "Funding Information: peptideb uilding blocks like 1 are currently underway.The results of these studieswill be reportedin due course. AcknowledgementsT:h is work was supportedb y WashingtonU niversity,the Pew Foundation, and the National Institutes of Health (Grant # PO1 GMZ4483-12).W e also gratefullya cknowledget he Washington University High Resolution NMR facility, partially supportedb y NIH lSlOR02004 and the Washington University Mass SpectrometryR esourceC enter,p artiallys upportedb y NIH RR00954f or their assistanceT.h e authorst hank Mr. Scott Rothfus for initially preparingi midesJ a and Sb and Mr. Daniel Sutherlinf or his help with the initial sodium borohydrider eductions. Referencesa nd Notes: a) For the designo f a numbero f analogss eeF ont, J. Ph.D. Thesis,W ashingtonU niversity in St. Louis, 1986.b ) For related syntheticm ethodologys tudiess ee Moeller, K. D.; Rothfus, S..L.; Wang, P. L. Tetrahedron1 991,4 7, 583. Moeller, K. D.; Rothfus, S. L. TetrahedronLe tt. 1992,3 3, 2913. For reviewso f reductiver outest o N-acyliminium ion formations eea) Zaugg,H . E. Synthesi1s 984,85, 181,b ) SpeckampW, . N.; Hiemstra,H . Tetrahedron1 985,41,4367a, nd c) SpeckampW, . N. Reel.T rav. Chem.P ays-Bas1 981,100,3 45. For a summarys ee reference3 b pages4 380-4381. a) Wijnberg, J. B. P. A.; Schoemaker,H . E.; Speckamp,W . N. Tetrahedron1 978,3 4, 179.F or an explanationo f this selectivitys ee Rosenfield Jr., R. E.; Dunitz, J. D. Helv. Chim. Acta 1978,6 1, 2176. Watanabe,T .; Hamaguchi,F .; Ohki, S. YakugakuZ asshi 1973,9 3, 845;C hem.A bstr. 1973,7 9,7 8328~. a) Hart, D. J.; Yang, T. K. J Chem.S ot. Chem. Commun.1 983,1 35a nd b) Chamberlin,A . R.; Chung, J. Y. L. J. Am. Chem. Sot. 1983,105,3 653. Nahasaka,T .; Tamano, H.; Hamaguchi,R . Heterocycle1s9 86,2 4, 1231. The regiochemistryo f the reduced products was assigned by determining the complete proton connectivityo f the moleculesw ith the use of 2D-COSY and HMQC experiments. 10. Das, G.; Thornton, E. R. J. Am. Chem.S ot. 1990,1 12,5 360a nd referencest herein.",
year = "1992",
month = oct,
day = "6",
doi = "10.1016/S0040-4039(00)60001-1",
language = "English",
volume = "33",
pages = "6041--6044",
journal = "Tetrahedron Letters",
issn = "0040-4039",
number = "41",
}