LETTER
Synthesis of Chiral Cyclic b-Amino Acids via Asymmetric Hydrogenation
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(13) Yields from the corresponding N-protected thiolactames:
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such as Boc.
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(20) Compound 4 was obtained as the pure E-isomer using the
reaction of a Peterson reagent (Me3SiCHLi-CO2Et) with the
N-protected d-lactone.
(21) Typical Procedures: Ruthenium: [(COD)Ru(2-
methylallyl)2] (0.01 mmol, 3.2 mg, 1 equiv) and (S,S)-MeO-
Biphep (0.012 mmol, 7 mg, 1.2 equiv) were stirred under
argon for 30 min in acetone (1 mL), 0.16 N HBr in MeOH
(140 mL, 2.2 equiv) was then slowly added and the solution
was stirred for 30 min at r.t. The unsaturated enamido ester
(100 equiv) was then added and the solution was transferred
into an autoclave. The autoclave was then purged three times
with hydrogen and filled with hydrogen at the required
pressure. The mixture was stirred at r.t. for 24 h. After
release of the hydrogen, the solvent was evaporated. The
residue was passed through a short silica gel plug to give the
reducted b-amino esters.
Rhodium: [(R,R)-(Me-DuPHOS)Rh(COD)(OTf)] (0.01
mmol, 6.6 mg, 1 equiv) was stirred under argon in degassed
CH2Cl2 (1 mL) at r.t. The unsaturated enamido ester (100
equiv) in CH2Cl2 was then added and the solution was
transferred into an autoclave and treated as previously
described.
Iridium: [(COD)Ir(Cl)]2 (0.05 mmol, 3.4 mg, 0.5 equiv) and
(S)-BINAP (0.012 mmol, 7.5 mg, 1.2 equiv) were stirred
under argon in a glass tube for 30 min in degassed CH2Cl2 (2
mL), the unsaturated enamido ester (100 equiv) was then
added, the glass tube was transferred into an autoclave and
treated as previously described.
Physical Data: compound 5: [a]D20 +58.5 (c 2.3, CH2Cl2),
ee: 97.3%. IR (KBr): 2955, 1737, 1698, 1452, 1385, 1194
cm–1. 1H NMR (200 MHz, CDCl3), two conformers: d =
1.23, 1.25 (2 t, 3 H, J = 7.1 and 7.2 Hz), 1.73–2.11 (m, 4 H),
2.01, 2.10 (2 s, 3 H), 2.31, 2.41, 2.54, 2.94 (4 dd, 2 × 2 H,
J = 3.9, 9.5, 15.4 and 3.6, 10.3, 15.4 Hz), 3.43 (m, 2 H), 4.12
(2 q, 2 H, J = 7.1 and 7.2 Hz), 4.23, 4.38 (2 m, 1 H). 13
C
NMR (50 MHz, CDCl3): d = 14.2, 23.0, 23.9, 30.1, 37.6,
47.9, 53.8, 60.4, 169.3, 171.5. MS (CI, NH3): m/z (%) = 217
Synlett 2004, No. 15, 2766–2770 © Thieme Stuttgart · New York