Tetrahedron

Asymmetric reactions of α-ketoacid-derived hemiacetals: Stereoselective synthesis of α-hydroxy acids

SV Pansare, RG Ravi

Index: Pansare, Sunil V.; Ravi, R. Gnana Tetrahedron, 1998 , vol. 54, # 48 p. 14549 - 14564

Full Text: HTML

Citation Number: 12

Abstract

N-Acylation of prolinol with α-ketoacid chlorides results in concomitant hemiacetalization of the α-keto amide by the prolinol hydroxyl group.(R) or (S) α-hydroxy acids are obtained with good enantiomeric excess by stereodivergent reduction of these hemiacetals. Reaction with Grignard reagents at ambient temperature furnishes (R) α-alkyl mandelic acids with good stereoselectivity.

Related Articles:

Synthetic studies of didemnins. IV. Synthesis of the macrocycle

[Ewing, William R.; Harris, Bruce D.; Li, Wen-Ren; Joullie, Madeleine M. Tetrahedron Letters, 1989 , vol. 30, # 29 p. 3757 - 3760]

Synthesis of new chiral ionic liquids from α-hydroxycarboxylic acids

[Poterala, Marcin; Plenkiewicz, Jan Tetrahedron Asymmetry, 2011 , vol. 22, # 3 p. 294 - 299]

Cationic BINAP-Ru (II) Halide Complexes: Highly Efficient Catalysts for Stereoselective Asymmetric Hydrogenation of. alpha.-and. beta.-Functionalized Ketones

[Mashima, Kazushi; Kusano, Koh-hei; Sato, Naomasa; Matsumura, Yoh-ichi; Nozaki, Kyoko; et al. Journal of Organic Chemistry, 1994 , vol. 59, # 11 p. 3064 - 3076]

… synthesis via organoboranes. 15. Selective reductions. 42. Asymmetric reduction of representative prochiral ketones with potassium 9-O-(1, 2: 5, 6-di-O-isopropylidene …

[Brown, Herbert C.; Cho, Byung Tae; Park, Won Suh Journal of Organic Chemistry, 1988 , vol. 53, # 6 p. 1231 - 1238]

Lyngbyabellins K–N from two Palmyra Atoll collections of the marine cyanobacterium Moorea bouillonii

[Choi, Hyukjae; Mevers, Emily; Byrum, Tara; Valeriote, Frederick A.; Gerwick, William H. European Journal of Organic Chemistry, 2012 , # 27 p. 5141 - 5150]

More Articles...