TY - JOUR
T1 - Enantioselective Synthesis of (-)-(7a S)-2,3,7,7a-Tetrahydro-7a- phenylthio-1 H -indene-1,5(6 H)-dione and (+)-(8a S)-3,4,8,8a-Tetrahydro-8a-phenylthio-1,6(2 H,7 H)-naphthalenedione
AU - Kwiatkowski, Stefan
AU - Syed, Ashfaq
AU - Brock, Carolyn P.
AU - Watt, David S.
N1 - Publisher Copyright:
© 1989 Georg Thieme Verlag. All rights reserved.
PY - 1989
Y1 - 1989
N2 - Application of the Hajos-Parrish asymetrically biased aldol condensation to 2-(3-oxobutyl)-2-phenylthio-1,3-cyclopentanedione (5a) or 2-(3-oxobutyl) -2-phenylthio-1,3-cyclohexanedione (5b) using (R)-(+)-proline provided (-)-(7aS)-2,3,7,7a-tetrahydro-7a-phenylthio-1H-indene -1,5(6H)-dione (7a) and (+)-(8aS)-3,4,8,8a-tetrahydro-8a -phenylthio-1,6(2H,7H)-naphthalenedione (7b), respectively, in = 95% enantiomeric excess, as determined by 1H-NMR analysis using tris[3-heptafluoropropylhydroxymethylene)-(+)-camphorato]europium(III).
AB - Application of the Hajos-Parrish asymetrically biased aldol condensation to 2-(3-oxobutyl)-2-phenylthio-1,3-cyclopentanedione (5a) or 2-(3-oxobutyl) -2-phenylthio-1,3-cyclohexanedione (5b) using (R)-(+)-proline provided (-)-(7aS)-2,3,7,7a-tetrahydro-7a-phenylthio-1H-indene -1,5(6H)-dione (7a) and (+)-(8aS)-3,4,8,8a-tetrahydro-8a -phenylthio-1,6(2H,7H)-naphthalenedione (7b), respectively, in = 95% enantiomeric excess, as determined by 1H-NMR analysis using tris[3-heptafluoropropylhydroxymethylene)-(+)-camphorato]europium(III).
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U2 - 10.1055/s-1989-27400
DO - 10.1055/s-1989-27400
M3 - Article
AN - SCOPUS:0002029115
SN - 0039-7881
VL - 1989
SP - 818
EP - 820
JO - Synthesis
JF - Synthesis
IS - 11
ER -