TY  - JOUR
AU  - Szakonyi, Zsolt
AU  - Balázs, Á
AU  - Martinek, Tamás
AU  - Fülöp, Ferenc
TI  - Stereoselective synthesis of pinane-based β- and γ-amino acids via conjugate addition of lithium amides and nitromethane
JF  - TETRAHEDRON-ASYMMETRY
J2  - TETRAHEDRON ASYMMETR
VL  - 21
PY  - 2010
IS  - 20
SP  - 2498
EP  - 2504
PG  - 7
SN  - 0957-4166
DO  - 10.1016/j.tetasy.2010.09.009
UR  - https://m2.mtmt.hu/api/publication/1413310
ID  - 1413310
N1  - Megjegyzés-21977629
Z9: 1
WC: Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chemistry, Physical
Funding Agency and Grant Number: Hungarian Research Foundation (OTKA)Orszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [NK81371]; Bolyai Janos Fellowships
            Funding text: We are grateful to the Hungarian Research Foundation (OTKA NK81371) for the financial support and acknowledge the receipt of Bolyai Janos Fellowships for Zsolt Szakonyi and Tamas A Martinek
CAplus AN 2010:1460524 (Journal);
AB  - Michael addition of dibenzylamine to (-)- and (+)-tert-butyl myrtenate, (-)-2 and (+)-2, derived from (-)- and (+)-myrtenal, furnished monoterpene-based β-amino acid derivatives in highly stereospecific reactions. The resultant amino esters (-)-3 and (+)-3 were transformed to unsubstituted, mono- and disubstituted and Fmoc-protected amino acids (-)-6-11 and (+)-6-11, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles. The microwave-assisted conjugate addition of nitromethane to α,β-unsaturated esters (-)-12 and (+)-12 likewise resulted in nitro esters (-)-13 and (+)-13 in highly stereospecific reactions. Compounds (-)-13 and (+)-13 were successfully transformed into γ-amino acids (-)-16 and (+)-16 in two steps. © 2010 Elsevier Ltd. All rights reserved.
LA  - English
DB  - MTMT
ER  -