Enantioselective Carbonyl Catalysis Enabled by Chiral Aldehydes

Wang, Qiang; Gu, Qianqun; You, Shu‐Li

doi:10.1002/ange.201808700

Cited by 29 publications

(5 citation statements)

References 66 publications

(18 reference statements)

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“…This well-defined strategy enabled asymmetric Mannich reaction of glycinate 6 with N -diphenylphosphinyl imines 7 in the presence of an N-quaternized pyridoxal catalyst, furnishing synthetically useful a , β -diamino acid esters 8 in high efficiency with remarkable stereocontrol. Since then, substantial research efforts culminated in a wide array of asymmetric transformations by exploiting chiral aldehydes as the reliable amine activation catalysts 24 .…”

Section: Development Of New Catalytic Strategiesmentioning

confidence: 99%

Advances in asymmetric organocatalysis over the last 10 years

2020

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Section: Development Of New Catalytic Strategiesmentioning

confidence: 99%

Advances in asymmetric organocatalysis over the last 10 years

2020

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“…Chiral aldehyde catalysis is a burgeoning strategy for the creation of novel asymmetric reactions of amines 20 – 25 , especially for the catalytic asymmetric α-functionalization of aminomethyl compounds 26 – 29 . However, only four reactions have been successfully realised using this strategy, all of which employed amino acids as the sole type of nucleophiles 30 – 33 .…”

Section: Introductionmentioning

confidence: 99%

Diastereodivergent chiral aldehyde catalysis for asymmetric 1,6-conjugated addition and Mannich reactions

Wen

Luo

et al. 2020

Nat Commun

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Chiral aldehyde catalysis is a burgeoning strategy for the catalytic asymmetric α-functionalization of aminomethyl compounds. However, the reaction types are limited and to date include no examples of stereodivergent catalysis. In this work, we disclose two chiral aldehyde-catalysed diastereodivergent reactions: a 1,6-conjugate addition of amino acids to para-quinone methides and a bio-inspired Mannich reaction of pyridinylmethanamines and imines. Both the syn- and anti-products of these two reactions can be obtained in moderate to high yields, diastereo- and enantioselectivities. Four potential reaction models produced by DFT calculations are proposed to explain the observed stereoselective control. Our work shows that chiral aldehyde catalysis based on a reversible imine formation principle is applicable for the α-functionalization of both amino acids and aryl methylamines, and holds potential to promote a range of asymmetric transformations diastereoselectively.

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“…As an emerging catalytic strategy, chiral aldehyde catalysis has been proven to be a good choice for the asymmetric α-functionalization of N-unprotected aminomethyl compounds. 6 The unique property of this strategy, producing amino-free products, provides a promising opportunity to introduce another transformation taking place at the amino site followed by the α-functionalization of amino acids for the construction of structurally diverse molecules. However, this strategy has not been well documented to date, and only two examples have been reported.…”

mentioning

confidence: 99%