Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using the modularly designed organocatalysts upon switching on their iminium catalysis

Pranjal Bora; Satish Jakkampudi; Ramarao Parella; Nagaraju Sakkani; Qipu Dai; Manisha Bihani; Hadi D. Arman; John C.G. Zhao

doi:10.1039/d1cc01020d

Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using the modularly designed organocatalysts upon switching on their iminium catalysis

Pranjal Bora, Satish Jakkampudi, Ramarao Parella, Nagaraju Sakkani, Qipu Dai, Manisha Bihani, Hadi D. Arman, John C.G. Zhao^*

^*Corresponding author for this work

University of Texas at San Antonio

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

The cinchona thiourea moiety in the self-assembled modularly designed organocatalysts (MDOs) switches off the iminium catalysis of these catalysts. In this study, it was found that the inhibited iminium catalysis could be switched on by using an appropriate weak acid and that, once the iminium catalysis was switched on, these catalysts could be applied for the highly stereoselective and diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes via a domino reaction between ketones and α,β-unsaturated aldehydes.

Original language	English
Article number	01020
Pages (from-to)	5334-5337
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	43
DOIs	https://doi.org/10.1039/d1cc01020d
Publication status	Published - 28 May 2021
Externally published	Yes

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title = "Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using the modularly designed organocatalysts upon switching on their iminium catalysis",

abstract = "The cinchona thiourea moiety in the self-assembled modularly designed organocatalysts (MDOs) switches off the iminium catalysis of these catalysts. In this study, it was found that the inhibited iminium catalysis could be switched on by using an appropriate weak acid and that, once the iminium catalysis was switched on, these catalysts could be applied for the highly stereoselective and diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes via a domino reaction between ketones and α,β-unsaturated aldehydes.",

author = "Pranjal Bora and Satish Jakkampudi and Ramarao Parella and Nagaraju Sakkani and Qipu Dai and Manisha Bihani and Arman, {Hadi D.} and Zhao, {John C.G.}",

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doi = "10.1039/d1cc01020d",

language = "English",

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T1 - Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using the modularly designed organocatalysts upon switching on their iminium catalysis

AU - Bora, Pranjal

AU - Jakkampudi, Satish

AU - Parella, Ramarao

AU - Sakkani, Nagaraju

AU - Dai, Qipu

AU - Bihani, Manisha

AU - Arman, Hadi D.

AU - Zhao, John C.G.

PY - 2021/5/28

Y1 - 2021/5/28

N2 - The cinchona thiourea moiety in the self-assembled modularly designed organocatalysts (MDOs) switches off the iminium catalysis of these catalysts. In this study, it was found that the inhibited iminium catalysis could be switched on by using an appropriate weak acid and that, once the iminium catalysis was switched on, these catalysts could be applied for the highly stereoselective and diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes via a domino reaction between ketones and α,β-unsaturated aldehydes.

AB - The cinchona thiourea moiety in the self-assembled modularly designed organocatalysts (MDOs) switches off the iminium catalysis of these catalysts. In this study, it was found that the inhibited iminium catalysis could be switched on by using an appropriate weak acid and that, once the iminium catalysis was switched on, these catalysts could be applied for the highly stereoselective and diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes via a domino reaction between ketones and α,β-unsaturated aldehydes.

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U2 - 10.1039/d1cc01020d

DO - 10.1039/d1cc01020d

M3 - Article

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AN - SCOPUS:85106968454

SN - 1359-7345

VL - 57

SP - 5334

EP - 5337

JO - Chemical Communications

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IS - 43

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ER -

Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using the modularly designed organocatalysts upon switching on their iminium catalysis

Abstract

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