Macrocyclization of terminal bis-allylic chlorides via an intramolecular gem-dialkylation of malononitrile or methyl cyanoacetate

Tetrahedron Letters

Volumn 39, Issue 43, 1998, Pages 7839-7840

  Chantigny, Yves ^a   Toró, András ^a   Lemelin, Charles A ^a   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

Alkylation; Coupling reagents; Cyano Compounds; Macrocycles

Indexed keywords

ACETIC ACID DERIVATIVE; CHLORIDE; MACROCYCLIC COMPOUND; MALONONITRILE; METHYL CYANOACETATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0032558661     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01722-5     Document Type: Article

References (6)

1. [1] Stowell JC. Carbanions in Organic Synthesis, First Edition, New York, John Wiley, 1979:210-212.
2. [2] Cope AC, Holmes HL, House HO. The Alkylation of Esters and Nitriles. Organic Reactions. New York: John Wiley, 1957;9:107-331.
3. [3] Campaigne E, Forsch RA. J. Org. Chem. 1978;43:1044-1050.
4. [4] The choice of base and solvents can favor dialkylation see: Ono N, Yoshimura T, Saito T, Tamura R, Tanikaga R, Kaji A. Bull. Chem. Soc. Jpn 1979;52:1716-1719.
5. 2). HR-MS: Calculated: 319.1783 found: 319.1789 ± 0.0010.
6. [6] In a trans-trans-trans system, a 10% yield of this macrocyclization is still competitive with the stepwise intermolecular bis-alkylation. Due to the formation of TADA products during the macrocyclization the characterization is difficult.