Improved Synthesis of N,N′‐Disuccinimidyl Carbonate using α‐Pinene as Acid Scavenger

Prasad, Maddipati; Nowshuddin, Shaik; Rao, Meena

doi:10.1080/00397910500281291

Cited by 5 publications

(1 citation statement)

References 12 publications

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“…Using an inorganic base such as Cs 2 CO 3 was ineffective for the transformation due to poor solubility, and significant unreacted starting material was observed (entry 6). When α-pinene was investigated as a scavenger to manage endogenous acid (entries 7–9), − the best overall combination of yield and enantioselectivity was observed using a 1:1 of DIPEA/pinene (entry 9). Reducing the reaction time to 4 h led to a corresponding decreased yield, confirming that 8–16 h is generally required (entry 10).…”

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confidence: 99%

Organocatalytic Asymmetric Synthesis of Si-Stereogenic Siloxanols

Dalton,

Bernal Sánchez,

Kelly

et al. 2024

ACS Catal.

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We report the organocatalytic synthesis of Si-stereogenic compounds via desymmetrization of a prochiral silanediol with a chiral imidazole-containing catalyst. This metal-free silylation method affords high yields with enantioselectivity up to 98:2 for various silanediol and silyl chloride substrate combinations (including secondary alkyl, vinyl, and H groups), accessing products with potential for further elaboration. NMR and X-ray studies reveal insight into the H-bonding interactions between the imidazole organocatalyst and the silanediol and the dual activating role of the Lewis basic imidazole to account for the high enantioselectivity.

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confidence: 99%