Direct derivatization of glyoxal into chiral templates providing complete discrimination between the aldehyde groups

Agami, Claude; Couty, François; Hamon, Louis; Prince, B.E.; Puchot, C.

doi:10.1016/s0040-4020(01)87885-6

Cited by 22 publications

(10 citation statements)

References 32 publications

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“…It has been assumed that the reaction proceeds via an iminium intermediate. [41d, f] N,S-acetals [48] are also well suited to the aminoalkylation of silyl enol ethers. An excellent 50] As has been demonstrated by Waldmann et al, other imines (from aldehydes and esters of amino acids) can also be used in the highly diastereoselective synthesis of dehydropiperidones.…”

Section: Reviewsmentioning

confidence: 99%

Modern Variants of the Mannich Reaction

Arend

Westermann

Risch

1998

Angewandte Chemie International Edition

1,088

362

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Important building blocks for the synthesis of drugs or natural products are found in Mannich bases and their derivatives. Modern variants of the Mannich reaction that expand the potential of the classical intermolecular reaction significantly and enable efficient control of the regioselectivity and stereoselectivity are therefore the topic of intensive research. Intramolecular reactions, in particular as part of domino reaction sequences, often afford astoundingly simple and elegant approaches to complex target compounds.

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Section: Reviewsmentioning

confidence: 99%

Modern Variants of the Mannich Reaction

Arend

Westermann

Risch

1998

Angewandte Chemie International Edition

1,088

362

View full text Add to dashboard Cite

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“…3,4,5-Trisubstituted morpholin-2-ol 246 was prepared by a condensation reaction between glyoxal (187), chiral 2aminoethanol 244 and thiophenol (243) 133 and further substitution of the thiophenol moiety in 245. When subjected to Swern oxidation, 246 yielded (3R,5R)-4-methyl-5-phenyl-3-propylmorpholin-2-one (247) as a precursor of N-methyl α-amino esters (Scheme 38).…”

Section: Scheme 37mentioning

confidence: 99%

Advances in the Synthesis of Morpholin-3-ones and Morpholin-2-ones

2012

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“…Agami et al [90,91] constructed various NMAs using the chiral morpholine 87 as a template (Scheme 6.29). By condensing N-methyl-D-phenylglycinol, glyoxal, and thiophenol, the morpholine 87 was obtained as a single stereoisomer [90].…”

Section: Asymmetric Synthesesmentioning

confidence: 99%

“…By condensing N-methyl-D-phenylglycinol, glyoxal, and thiophenol, the morpholine 87 was obtained as a single stereoisomer [90]. Treating the morpholine 87 with organometallic reagents displaces the thiophenyl ether moiety in a stereocontrolled fashion with excellent control, giving in most cases above 98% e.e.…”

Section: Asymmetric Synthesesmentioning

confidence: 99%