Tetrahedron

Lactam & amide acetals XXI. Use of pyroglutamic acid and proline in chiral synthesis of conformationally constrained piperazinones

…, K Sujatha, KVR Krishna, R Roy, J Singh, N Anand

Index: Jain, Sanjay; Sujatha; Rama Krishna; Roy, Raja; Singh, Jujhar; Anand, Nitya Tetrahedron, 1992 , vol. 48, # 23 p. 4985 - 4998

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Citation Number: 25

Abstract

Making use of amide activation chiral synthesis of (+)-(1S, 5R)-and (−)-(1R, 5S)-3, 8- diazabicyclo [3.2. 1] octan-2-ones (1 and 2) has been achieved from L-and D- pyroglutamates, and of (−)-(2R, 6S)-,(−)-(2S, 6S)-,(+)-(2s, 6R)-and (+)-(2R, 6R)-2-methyl-1, 4- diazabicyclo [4.3. 0] nonan-5-ones (3 a, 3 b, 4 a and 4 b) from L & D-proline methyl esters respectively. The key step of the synthesis involves a stereo-selective catalytic ...