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Diastereoselective Addition of Allyl Reagents to Variously N ‐Monoprotected and N , N ‐Diprotected L ‐Alaninals
Author(s) -
Gryko Dorota,
Jurczak Janusz
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20001004)83:10<2705::aid-hlca2705>3.0.co;2-y
Subject(s) - chemistry , diastereomer , reagent , allyl bromide , aqueous solution , bromide , elongation , stereochemistry , medicinal chemistry , organic chemistry , materials science , metallurgy , ultimate tensile strength
Diastereoselective C 3 ‐elongation processes of N ‐Boc‐, N ‐Z‐, N ‐Bn‐ N ‐Boc‐, and N ‐Bn‐ N ‐Z‐ L ‐alaninals (Boc= t BuOCO, Z=PhCH 2 OCO, Bn=PhCH 2 ) using various allyl reagents, such as allyl bromide in the presence of Zn/aqueous NH 4 Cl solution, of SnCl 2 ⋅2 H 2 O/NaI or of Mg/CuCl 2 ⋅2 H 2 O, as well as allyltrichlorosilane, are described. A substantially different influence of the N ‐protecting groups replacing either one or two amino protons was observed, allowing the selective synthesis of either the syn ‐ or anti ‐diastereoisomer as a major product.