Synthesis of D-Fructose-Based Bifunctional Primary Amine-Thiourea Organocatalysts and Their Applications in Asymmetric Reactions

Author:

Lalhmangaihzuala Samson12ORCID,Khiangte Vanlalngaihawma12,Laldinpuii Zathang12ORCID,Nunnemi Lal12,Malsawmsanga Joute12,Lallawmzuali Gospel13,Liana Thanhming1,Lalhriatpuia Chhakchhuak1,Pachuau Zodinpuia2,Vanlaldinpuia Khiangte1

Affiliation:

1. Department of Chemistry, Pachhunga University College, Mizoram University, Aizawl 796001, Mizoram, India

2. Department of Chemistry, Mizoram University, Tanhril, Aizawl 796004, Mizoram, India

3. Department of Environmental Science, Mizoram University, Tanhril, Aizawl 796004, Mizoram, India

Abstract

The preparation of a new class of six bifunctional thiourea organocatalysts having a D-fructose scaffold and a primary amino group was demonstrated. In the present study, the novel organocatalysts exhibited excellent enantio- and moderate diastereoselectivities in the asymmetric Michael addition of aliphatic ketones and 1,3-diketone to substituted nitroolefins at room temperature. In addition, the direct asymmetric aldol reaction between cyclic aliphatic ketone and aromatic aldehydes was also studied in the presence of the saccharide-thiourea organocatalysts giving excellent yield with moderate enantioselectivity.

Funder

Science and Engineering Research Board

Publisher

MDPI AG

Subject

Organic Chemistry,Inorganic Chemistry,Electrochemistry,Chemistry (miscellaneous)

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