- Enantioselective Formal α-Methylation and α-Benzylation of Aldehydes by Means of Photo-organocatalysis
-
Detailed herein is the photochemical organocatalytic enantioselective α-alkylation of aldehydes with (phenylsulfonyl)alkyl iodides. The chemistry relies on the direct photoexcitation of enamines to trigger the formation of reactive carbon-centered radicals from iodosulfones, while the ground-state chiral enamines provide effective stereochemical control over the radical trapping process. The phenylsulfonyl moiety, acting as a redox auxiliary group, facilitates the generation of radicals. In addition, it can eventually be removed under mild reducing conditions to reveal methyl and benzyl groups.
- Filippini, Giacomo,Silvi, Mattia,Melchiorre, Paolo
-
supporting information
p. 4447 - 4451
(2017/04/13)
-
- Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand
-
A rhodium complex, in conjunction with commercially available Ph-BPE ligand, catalyzes the branch-selective asymmetric hydroformylation of 1-alkenes and rapidly generates α-chiral aldehydes. A wide range of terminal olefins including 1-dodecene were examined, and all delivered high enantioselectivity (up to 98:2 er) as well as good branch:linear ratios (up to 15:1). (Chemical Equation Presented).
- Yu, Zhiyong,Eno, Meredith S.,Annis, Alexandra H.,Morken, James P.
-
supporting information
p. 3264 - 3267
(2015/07/15)
-
- Synthesis of homopropargyl alcohols via insertion of allenyl carbenoids into acyclic organozirconium bonds
-
Insertion of allenyl carbenoids (3-tosyloxy-1-lithioalk-1-ynes) into organozirconium complexes gave allenyl-zirconocenes via a 1,2-zirconate rearrangement. Trapping of the allenyl-zirconium species with aldehydes and ketones gave, after hydrolysis, a seri
- Stec, Jozef,Henderson, Alan R.,Whitby, Richard J.
-
scheme or table
p. 1112 - 1115
(2012/03/26)
-
- Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction
-
(Chemical Equation Presented) A convergent total synthesis of khafrefungin was accomplished on the basis of (1) the highly stereoselective TiCl 4-mediated vinylogous Mukaiyama aldol reaction using vinylketene silyl N,O-acetal and (2) syn-select
- Shirokawa, Shin-Ichi,Shinoyama, Mariko,Ooi, Isao,Hosokawa, Seijiro,Nakazaki, Atsuo,Kobayashi, Susumu
-
p. 849 - 852
(2007/10/03)
-
- Chemistry and biology of khafrefungin. Large-scale synthesis, design, and structure-activity relationship of khafrefungin, an antifungal agent
-
Large-scale synthesis, design, and structure-activity relationships of khafrefungin are reported. Khafrefungin is an antifungal agent that inhibits inositol phosphorylceramide (IPC) synthase, a enzyme involved in fungal sphingolipid biosynthesis. Unlike o
- Nakamura, Masayuki,Mori, Yuichiro,Okuyama, Kennichi,Tanikawa, Kunihiro,Yasuda, Satoshi,Kanada, Kentaro,Kobayashi, Shu
-
p. 3362 - 3376
(2007/10/03)
-
- Efficient total synthesis of khafrefungin: Convergent approach using Suzuki coupling under thallium-free conditions toward multigram-scale synthesis
-
An efficient and practical synthetic route to khafrefungin, an antifungal agent, has been developed based on successive coupling of three components, 3, 4, and then 2. A key step of the synthesis is the Suzuki coupling of 2 and 10, in which the use of tox
- Mori, Yuichiro,Nakamura, Masayuki,Wakabayashi, Takeshi,Mori, Kouhei,Kobayashi, Shu
-
p. 601 - 603
(2007/10/03)
-
- Total synthesis and structural elucidation of khafrefungin
-
Total synthesis and structural elucidation of khafrefungin, a novel antifungal agent isolated from the fermentation culture MF6020, have been achieved. Unlike other inhibitors that inhibit the corresponding enzyme in fungi and mammals to the same extent,
- Wakabayashi,Mori,Kobayashi
-
p. 1372 - 1375
(2007/10/03)
-
- Generation of chiral (η5-indenyl)2(η3-allyl)Ti complex and its highly enantioselective reaction with carbonyl compounds
-
The (η5-indenyl)2(η3-2-alkyl-1-methylallyl)Ti complex 10, successfully generated from (η5-indenyl)2TiCl2 8, 2-alkylbutadiene, and i-PrMgCl, reached with carbon dioxide or RCHO (R = Ph, ET, i-Pr, or t-Bu) to give the corresponding optically active β,γ-unsaturated carboxylic acid 11 or threohomoallyl alcohols 12-15 with high enantiomeric purities of up to 96%.
- Urabe, Hirokazu,Yoshikawa, Kaoru,Sato, Fumie
-
p. 5595 - 5598
(2007/10/03)
-