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Volumn , Issue 18, 2007, Pages 2829-2832

Michael addition of manganese enolates to nitroolefins

Author keywords

Enolates; Manganese; Michael addition; Nitroolefins; Selectivity

Indexed keywords

ALKENE DERIVATIVE; KETONE; MANGANESE; THIOUREA;

ARTICLE; MICHAEL ADDITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 36649034501 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-991096 Document Type: Article

Times cited : (18)

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29
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- General Procedure for the Preparation of Enolates via Manganese Enamides: To a suspension of LiBr (417 mg, 4.8 mmol) in freshly distilled THF (6 mL) in a 3-necked 25-mL round-bottomed flask under argon, MnBr 2 (516 mg, 2.4 mmol) was introduced and the solution was stirred until complete dissolution (transparent pale yellow solution, After addition of n-butylaniline (380 μL, 2.4 mmol) the temperature was cooled to -20°C and methyllithium (3 mL, 4.8 mmol) was introduced dropwise. On keeping the temperature under 0°C, the solution became limpid and red-dark colored after 10 min. The desired ketone (2 mmol) was then slowly added keeping the temperature between -10°C and 10°C. All the Mn enolates were formed in 30 min at this temperature. General Procedure for Michael Addition of Manganese Enolates to Nitroalkenes: The nitroalkenes (1.15 equiv) were added to the enolate solution at the required temperature without previous dissolution. The
- 2 = 7.2 Hz, 1 H).

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