Solid state asymmetric synthesis of chiral crystals of 5- and 7-membered ring ketones

Enantioselective synthesis of cyclobutane derivatives is still a challenging topic in asymmetric synthesis. [2+2]-Cycloaddition and skeleton rearrangement are two primary strategies to this end. Recently, functionalization of cyclobutanones and cyclobutenones, which are readily available via [2+2]-cycloadditions as prochiral substrates, has emerged as a powerful tool to access versatile four-membered ring compounds. Herein, we summarize some recent advances in these areas from our and other groups.

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Absolute Asymmetric Synthesis by Irradiation of Chiral Crystals

Organic Synthesis Set ◽

10.1002/9783527620784.ch16b ◽

2003 ◽

pp. 89-95

Author(s):

Gerd Kaupp ◽

Michael Haak

Keyword(s):

Asymmetric Synthesis ◽

Absolute Asymmetric Synthesis ◽

Chiral Crystals

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Ionic chiral handle-induced asymmetric synthesis in a solid state Norrish type II photoreaction

Tetrahedron Asymmetry ◽

10.1016/0957-4166(94)80099-5 ◽

1994 ◽

Vol 5 (8) ◽

pp. 1415-1418 ◽

Cited By ~ 24

Author(s):

H. Koshima ◽

A. Maeda ◽

N. Masuda ◽

T. Matsuura ◽

K. Hirotsu ◽

...

Keyword(s):

Solid State ◽

Asymmetric Synthesis ◽

Type Ii ◽

Norrish Type

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Asymmetric Synthesis of Six-Membered Ring Nitrogen Heterocycles with More Than One Heteroatom

Asymmetric Synthesis of Nitrogen Heterocycles ◽

10.1002/9783527625505.ch7 ◽

2009 ◽

pp. 293-366 ◽

Cited By ~ 3

Author(s):

Pter Mtyus ◽

Pl Tpolcsanyi

Keyword(s):

Asymmetric Synthesis ◽

Nitrogen Heterocycles ◽

Membered Ring ◽

Ring Nitrogen

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Macrocyclic Gold(I) Complexes with Bridging Diacetylide and Diphosphine Ligands

Zeitschrift für Naturforschung B ◽

10.1515/znb-2004-11-1219 ◽

2004 ◽

Vol 59 (11-12) ◽

pp. 1488-1496 ◽

Cited By ~ 2

Author(s):

William J. Hunks ◽

Michael C. Jennings ◽

Richard J. Puddephatt

Keyword(s):

Solid State ◽

Membered Ring ◽

Diphosphine Ligands

The new dialkynyldigold(I) complexes [Ar(OCH2C≡CAu)2]n {Ar = 1,4-C6H4(CMe2-4-C6H4)2, 4,4’-C6H4C6H4 and 1,5-C10H6} react with diphosphines LL = Ph2P(CH2)nPPh2 (n = 1 to 6) and trans-Ph2PCH=CHPPh2 to give luminescent macrocyclic digold(I) or tetragold(I) complexes with bridging diphosphine and diacetylide ligands. The digold(I) complex [1,4-C6H4(CMe2-4- C6H4OCH2C≡CAu)2(μ-LL)], with LL = trans-Ph2PCH=CHPPh2, forms a 28-membered ring, and the rings associate through aurophilic bonding in the solid state. In contrast, the tetragold(I) complex [4,4’-C6H4C6H4(OCH2C≡CAu)2(μ-LL)], with LL = Ph2PCH2PPh2, forms a more rigid 42-membered ring.

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