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Abstract The diastereodivergent synthesis of bridged 1,2,3,4‐tetrahydroisoquinoline derivatives has been achieved by using appropriate modularly designed organocatalysts (MDOs) that are self‐assembled in situ from amino acids and cinchona alkaloid derivatives. The domino Mannich/aza‐Michael/aldol reaction between (E)‐2‐[2‐(3‐aryl‐3‐oxoprop‐1‐en‐1‐yl)phenyl]acetaldehydes and ethyl or benzyl (E)‐2‐[(4‐methoxyphenyl)imino]acetates catalyzed by MDOs gives two different diastereomers of the desired bridged tetrahydroisoquinolines in good yields and excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to >99%ee). The diastereodivergence was achieved in the aldol reaction step. magnified image
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Recent Progress in Organocatalytic Asymmetric Domino Transformations
Abstract Sustainability in chemical synthesis is a major aspect of the current synthetic endeavors and, therefore, mimicking the biological process in the laboratory nowadays has the highest priority. Towards achieving this goal, designing organic reactions in domino mode rather than the multistep synthetic pathways and using organocatalysis instead of metal catalysis have received a lot of attention due to the inherent advantages of these processes in terms of synthetic efficiency and sustainability. As a result, the field of asymmetric organocatalytic domino reactions has witnessed tremendous progress in recent years. This review attempts to summarize the latest developments in asymmetric organocatalyzed domino reactions since 2012, with the emphasis on the catalysts and reaction modes. Discussions on the reaction mechanisms and the applications of the developed domino reaction methods in the synthesis of biologically active molecules and natural products are also included when appropriate. magnified image
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- Award ID(s):
- 1664278
- PAR ID:
- 10046797
- Publisher / Repository:
- Wiley Blackwell (John Wiley & Sons)
- Date Published:
- Journal Name:
- Advanced Synthesis & Catalysis
- Volume:
- 360
- Issue:
- 1
- ISSN:
- 1615-4150
- Format(s):
- Medium: X Size: p. 2-79
- Size(s):
- p. 2-79
- Sponsoring Org:
- National Science Foundation
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