Unknown

Dataset Information

0

Reactivity of (1-methoxycarbonylpentadienyl)iron(1+) cations with hydride, methyl, and nitrogen nucleophiles.


ABSTRACT: The reaction of tricarbonyl and (dicarbonyl)triphenylphosphine (1-methoxycarbonyl-pentadientyl)iron(1+) cations 7 and 8 with methyl lithium, NaBH3CN, or potassium phthalimide affords (pentenediyl)iron complexes 9a-c and 11a-b, while reaction with dimethylcuprate, gave (E,Z-diene)iron complexes 10 and 12. Oxidatively induced-reductive elimination of 9a-c gave vinylcyclopropanecarboxylates 17a-c. The optically active vinylcyclopropane (+)-17a, prepared from (1S)-7, undergoes olefin cross-metathesis with excess (+)-18 to yield (+)-19, a C9-C16 synthon for the antifungal agent ambruticin. Alternatively reaction of 7 with methanesulfonamide or trimethylsilylazide gave (E,E-diene)iron complexes 14d and e. Huisgen [3+2] cyclization of the (azidodienyl)iron complex 14e with alkynes afforded triazoles 25a-e.

SUBMITTER: Ma Y 

PROVIDER: S-EPMC5703425 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

altmetric image

Publications

Reactivity of (1-methoxycarbonylpentadienyl)iron(1+) cations with hydride, methyl, and nitrogen nucleophiles.

Ma Yuzhi Y   Yun Young K YK   Wondergem Nee Lukesh Julie J   Sar Anobick A   Gone Jayapal Reddy JR   Lindeman Sergey S   Donaldson William A WA  

Tetrahedron 20170615 30


The reaction of tricarbonyl and (dicarbonyl)triphenylphosphine (1-methoxycarbonyl-pentadientyl)iron(1+) cations <b>7</b> and <b>8</b> with methyl lithium, NaBH<sub>3</sub>CN, or potassium phthalimide affords (pentenediyl)iron complexes <b>9a-c</b> and <b>11a-b</b>, while reaction with dimethylcuprate, gave (<i>E</i>,<i>Z</i>-diene)iron complexes <b>10</b> and <b>12</b>. Oxidatively induced-reductive elimination of <b>9a-c</b> gave vinylcyclopropanecarboxylates <b>17a-c</b>. The optically active  ...[more]

Similar Datasets

| S-EPMC5898444 | biostudies-literature
| S-EPMC5536248 | biostudies-literature
| S-EPMC4038673 | biostudies-literature
| S-EPMC6540918 | biostudies-literature
| S-EPMC9814260 | biostudies-literature
| S-EPMC8456786 | biostudies-literature
| S-EPMC5653312 | biostudies-literature
| S-EPMC5809131 | biostudies-literature
| S-EPMC4662568 | biostudies-literature
| S-EPMC4833004 | biostudies-literature