New Chiral Auxiliaries for Enolate Alkylations

Kyu‐Sung ‐S Jeong; Kevin Parris; Pablo Ballester; Julius Rebek

doi:10.1002/anie.199005551

New Chiral Auxiliaries for Enolate Alkylations

Kyu‐Sung ‐S Jeong, Kevin Parris, Pablo Ballester, Julius Rebek

Department of Chemistry

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

31 Citations (Scopus)

Abstract

The stereospecific synthesis (>99:1) of α‐alkylcarboxylic acids 3 has been achieved using chiral auxiliaries such as 1, which is a derivative of the Kemp triacid. Compound 1 is coupled at the imide group with the acid chloride 2. Lithiation (→enolate), alkylation, and cleavage leads to 3. The effectiveness of 1 is a consequence of the fact that it shields one side of the enolate from attack by the electrophile EX (examples: R  Me, E  PhCH₂, or R  PhCH₂, E  Me). (Figure Presented.)

Original language	English
Pages (from-to)	555-556
Number of pages	2
Journal	Angewandte Chemie International Edition in English
Volume	29
Issue number	5
DOIs	https://doi.org/10.1002/anie.199005551
Publication status	Published - 1990 May

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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title = "New Chiral Auxiliaries for Enolate Alkylations",

abstract = "The stereospecific synthesis (>99:1) of α‐alkylcarboxylic acids 3 has been achieved using chiral auxiliaries such as 1, which is a derivative of the Kemp triacid. Compound 1 is coupled at the imide group with the acid chloride 2. Lithiation (→enolate), alkylation, and cleavage leads to 3. The effectiveness of 1 is a consequence of the fact that it shields one side of the enolate from attack by the electrophile EX (examples: R  Me, E  PhCH2, or R  PhCH2, E  Me). (Figure Presented.)",

author = "Jeong, {Kyu‐Sung ‐S} and Kevin Parris and Pablo Ballester and Julius Rebek",

year = "1990",

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T1 - New Chiral Auxiliaries for Enolate Alkylations

AU - Jeong, Kyu‐Sung ‐S

AU - Parris, Kevin

AU - Ballester, Pablo

AU - Rebek, Julius

PY - 1990/5

Y1 - 1990/5

N2 - The stereospecific synthesis (>99:1) of α‐alkylcarboxylic acids 3 has been achieved using chiral auxiliaries such as 1, which is a derivative of the Kemp triacid. Compound 1 is coupled at the imide group with the acid chloride 2. Lithiation (→enolate), alkylation, and cleavage leads to 3. The effectiveness of 1 is a consequence of the fact that it shields one side of the enolate from attack by the electrophile EX (examples: R  Me, E  PhCH2, or R  PhCH2, E  Me). (Figure Presented.)

AB - The stereospecific synthesis (>99:1) of α‐alkylcarboxylic acids 3 has been achieved using chiral auxiliaries such as 1, which is a derivative of the Kemp triacid. Compound 1 is coupled at the imide group with the acid chloride 2. Lithiation (→enolate), alkylation, and cleavage leads to 3. The effectiveness of 1 is a consequence of the fact that it shields one side of the enolate from attack by the electrophile EX (examples: R  Me, E  PhCH2, or R  PhCH2, E  Me). (Figure Presented.)

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