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The method to separate inidividual phosphinic dipeptide stereoisomers using HPLC was reported, see: Mucha, A.; Lammerhofer, M.; Lindner, W.; Pawelczak, M.; Kafarski, P. Bioorg. Med. Chem. Lett. 2008, 18, 1550.
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For application of our methodology to the synthesis of α,α′-diaminophosphinates and α-amino-α′- hydroxyphosphinates, see: a
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For application of our methodology to the synthesis of α,α′-diaminophosphinates and α-amino-α′- hydroxyphosphinates, see: (a) Kaboudin, B.; Haruki, T.; Yamagishi, T.; Yokomatsu, T. Tetrahedron 2007, 63, 8199.
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Alkylation of lithiun enolates derived from γ-amino esters and δ-hydroxy esters was reported to proceed with high diastereoselectivity. In these cases, selectivity were rationalized by cis-enolates bearing a cyclic chelated structure. Reactions of γ-amino esters: (a) Hanessian, S, Schaum, R. Tetrahedron Lett. 1997, 38, 163
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Alkylation of lithiun enolates derived from γ-amino esters and δ-hydroxy esters was reported to proceed with high diastereoselectivity. In these cases, selectivity were rationalized by cis-enolates bearing a cyclic chelated structure. Reactions of γ-amino esters: (a) Hanessian, S.; Schaum, R. Tetrahedron Lett. 1997, 38, 163.
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A similar benzylation of 14 was also attempted using LiCl (6 equiv) as an additive, which has previously been elucidated to enhance the reactivity of lithium enolates and have an influence on the diastereoselectivity of their alkylation reactions by changing the aggregated states. However, the selectivity was deteriorated to 21a:21b = 3:1. For LiCl-mediated reactions of lithium enolates with electrophiles, see: (a) Seebach, D.; Grundler, H.; Shoda, S.-I. Helv. Chim. Acta 1991, 74, 197.
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A similar benzylation of 14 was also attempted using LiCl (6 equiv) as an additive, which has previously been elucidated to enhance the reactivity of lithium enolates and have an influence on the diastereoselectivity of their alkylation reactions by changing the aggregated states. However, the selectivity was deteriorated to 21a:21b = 3:1. For LiCl-mediated reactions of lithium enolates with electrophiles, see: (a) Seebach, D.; Grundler, H.; Shoda, S.-I. Helv. Chim. Acta 1991, 74, 197.
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2-mediated removal of the sulfonyl group of N-benzoyl benzenesulfonamide derivatives, see: Knowles, H.; Parsons, A. F.; Pettifer, R. M. Synlett. 1997, 271.
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