| Record 11660 View: Standard | Glossary HistCite Guide |
|
Author(s): Shi FQ; Song BA
Title: Origins of enantioselectivity in the chiral Bronsted acid catalyzed hydrophosphonylation of imines
Source: ORGANIC & BIOMOLECULAR CHEMISTRY 7 (7): 1292-1298
Date: 2009
Document Type: Journal : Review
DOI:
Language: English
Comment:
Address: Guizhou Univ, Ctr Res & Dev Fine Chem, Minist Educ, Key Lab Green Pesticide & Agr Bioengn, Guiyang 550025, Peoples R China.
Reprint: Shi, FQ, Guizhou Univ, Ctr Res & Dev Fine Chem, Minist Educ, Key Lab
Green Pesticide & Agr Bioengn, Guiyang 550025, Peoples R China. E-mail: fcc.fqshi@gzu.edu.cn
Author Keywords:
KeyWords Plus: ALPHA-AMINO PHOSPHONATES; FRIEDEL-CRAFTS REACTION; PHASE-TRANSFER
CATALYSIS; MANNICH-TYPE REACTION; DIELS-ALDER REACTION; POLARIZABLE
CONTINUUM MODEL; BAYLIS-HILLMAN REACTION; ASYMMETRIC-SYNTHESIS;
PHOSPHORIC-ACID; TRANSFER HYDROGENATION
Abstract: The results of an experimental and ONIOM-based computational investigation of the mechanism and the origins of enantioselectivity in the asymmetric synthesis of alpha-amino phosphonates by an enantioselective hydrophosphonylation of imines catalyzed by chiral Bronsted acids are reported. It was found that the enantioselectivity observed in the enantioselective hydrophosphonylation of the imine with a benzothiazole moiety was poor. A detailed computational study with a two-layer ONIOM (B3LYP/6-31G(d)/AM1) method on the mechanism of the investigated reaction was carried out to explore the origins of the enantioselectivity. Calculations indicate that the investigated reaction is a two-step process involving proton-transfer and nucleophilic addition, which is the stereo-controlling step. The investigated reaction prefers a di-coordination pathway to a mono-coordination pathway. The different enantioselectivities exhibited by three kinds of catalyst and two kinds of nucleophile were rationalized. Calculations indicate that si-facial attack is higher in energy than re-facial attack by only 0.1 kcal/mol, which accounts well for the low ee value observed in the enantioselective hydrophosphonylation of the imine with a benzothiazole moiety. The energy barrier for phosphonate-phosphite tautomerism catalyzed by chiral Bronsted acid in toluene is only 1.8 kcal/mol, which could explain why the investigated reaction can take place at room temperature.
Cited References: AKIYAMA T, 2004, ANGEW CHEM INT EDIT, V43, P1566 AKIYAMA T, 2005, ORG LETT, V7, P2583 AKIYAMA T, 2006, ADV SYNTH CATAL, V348, P999 AKIYAMA T, 2006, SYNLETT 0105, P141 AKIYAMA T, 2008, ADV SYNTH CATAL, V350, P399 ANKE JRH, 1996, J AM CHEM SOC, V118, P6031 BADER RFW, 1984, J CHEM PHYS, V80, P1943 BADER RFW, 1990, ATOMS MOL QUANTUM TH BARONE V, 1998, J COMPUT CHEM, V19, P404 BIEGLERKONIG F, 2001, J COMPUT CHEM, V22, P545 BIEGLERKONIG F, 2002, J COMPUT CHEM, V23, P1489 BOLM C, 2005, ANGEW CHEM INT EDIT, V44, P1758 CHEN XH, 2006, J AM CHEM SOC, V128, P14802 CHEONG PHY, 2004, J AM CHEM SOC, V126, P13912 CLEMENTE FR, 2005, J AM CHEM SOC, V127, P11294 CONNON SJ, 2006, ANGEW CHEM INT EDIT, V45, P3909 DAPPRICH S, 1999, J MOL STRUC-THEOCHEM, V461, P1 DAVIS FA, 2001, ORG LETT, V3, P1757 DEJUGNAT C, 2003, CHEM COMMUN, P1858 DENG W, 2006, J MOL STRUC-THEOCHEM, V775, P93 DESIMONI G, 2006, CHEM REV, V106, P3561 DEWAR MJS, 1985, J AM CHEM SOC, V107, P3902 DIELTIENS N, 2006, CHEM-EUR J, V13, P203 FAZA ON, 2006, J AM CHEM SOC, V128, P2434 FRISCH MJ, 1998, GAUSSIAN98 REVISION GRIDNEV ID, 2007, TETRAHEDRON LETT, V48, P497 GROEGER H, 1996, TETRAHEDRON LETT, V37, P9291 GROEGER H, 1998, J AM CHEM SOC, V120, P3089 GROGER H, 2003, CHEM REV, V103, P2795 GUO QX, 2007, J AM CHEM SOC, V129, P3790 HAMMERSCHMIDT F, 2000, J ORG CHEM, V65, P6121 HIRSCHMANN R, 1994, SCIENCE, V265, P234 HU DY, 2008, J AGR FOOD CHEM, V56, P998 HUANG Y, 2003, NATURE, V424, P146 ITOH J, 2006, ANGEW CHEM INT EDIT, V45, P4796 ITOH J, 2008, ANGEW CHEM INT EDIT, V47, P4016 JIN LH, 2006, BIOORG MED CHEM LETT, V16, P1537 JOLY GD, 2004, J AM CHEM SOC, V126, P4102 KAFARSKI P, 1991, PHOSPHORUS SULFUR, V63, P193 KAFARSKI P, 2001, CURR MED CHEM ANTICA, V1, P301 KANG Q, 2007, ADV SYNTH CATAL, V349, P1657 KANG Q, 2007, J AM CHEM SOC, V129, P1484 KANG Q, 2008, CHEM-EUR J, V14, P3539 KANG Q, 2008, ORG LETT, V10, P2031 KIZIRIAN JC, 2008, CHEM REV, V108, P140 KOBAYASHI S, 2004, J AM CHEM SOC, V126, P6558 KOLODIAZHNYI OI, 1998, TETRAHEDRON-ASYMMETR, V9, P1279 LEFEBVRE IM, 1997, J ORG CHEM, V62, P7532 LINTUNEN T, 2000, BIOORG MED CHEM LETT, V10, P1749 LIU H, 2006, ORG LETT, V8, P6023 LIU WS, 2002, BIOCHEMISTRY-US, V41, P12320 LYGO B, 2004, ACCOUNTS CHEM RES, V37, P518 MA JA, 2003, ANGEW CHEM INT EDIT, V42, P4290 MARUOKA K, 2003, CHEM REV, V103, P3013 MATSUI K, 2005, J AM CHEM SOC, V127, P3680 MCDOUGAL NT, 2003, J AM CHEM SOC, V125, P12094 MCDOUGAL NT, 2004, ADV SYNTH CATAL, V346, P1231 MITSUMORI S, 2006, J AM CHEM SOC, V128, P1040 MOMIYAMA N, 2005, J AM CHEM SOC, V127, P1080 NIETOOBERHUBER C, 2004, ANGEW CHEM INT EDIT, V43, P2402 NIETOOBERHUBER C, 2005, ANGEW CHEM INT EDIT, V44, P6146 NIETOOBERHUBER C, 2006, CHEM-EUR J, V12, P5916 NIU SQ, 2000, CHEM REV, V100, P353 NUGENT BM, 2004, J AM CHEM SOC, V126, P3418 ODONNELL MJ, 2004, ACCOUNTS CHEM RES, V37, P506 OKINO T, 2003, J AM CHEM SOC, V125, P12672 OLSZEWSKI TK, 2006, TETRAHEDRON, V62, P2183 PATEL DV, 1995, J MED CHEM, V38, P4557 PIHKO PM, 2004, ANGEW CHEM INT EDIT, V43, P2062 PONS JM, 1997, J AM CHEM SOC, V119, P3333 POPELIER PLA, 1998, J PHYS CHEM A, V102, P1873 RUEPING M, 2005, ORG LETT, V7, P3781 RUEPING M, 2006, ANGEW CHEM INT EDIT, V45, P2617 RUEPING M, 2006, ANGEW CHEM INT EDIT, V45, P3683 RUEPING M, 2006, ANGEW CHEM INT EDIT, V45, P6751 RUEPING M, 2006, ANGEW CHEM INT EDIT, V45, P7832 RUEPING M, 2007, ADV SYNTH CATAL, V349, P759 RUEPING M, 2007, ANGEW CHEM INT EDIT, V46, P2097 RUEPING M, 2007, ORG LETT, V9, P1065 RUEPING M, 2008, ANGEW CHEM INT EDIT, V47, P593 SASAI H, 1995, J ORG CHEM, V60, P6656 SCHLEMMINGER I, 2000, J ORG CHEM, V65, P4818 SCHREINER PR, 2003, CHEM SOC REV, V32, P289 SHI FQ, 2007, J AM CHEM SOC, V129, P15503 SMITH AB, 1995, J AM CHEM SOC, V117, P10879 SMITH WW, 1998, J AM CHEM SOC, V120, P4622 SOBCZYK L, 2005, CHEM REV, V105, P3513 SOLA M, 1996, J AM CHEM SOC, V118, P8920 SONG BA, 2003, MOLECULES, V8, P186 STOWASSER B, 1992, TETRAHEDRON LETT, V33, P6625 TAKANO Y, 2005, J CHEM THEORY COMPUT, V1, P70 TAYLOR MS, 2006, ANGEW CHEM INT EDIT, V45, P1520 TERADA M, 2006, ANGEW CHEM INT EDIT, V45, P2254 TERADA M, 2007, ADV SYNTH CATAL, V349, P1863 TERADA M, 2007, J AM CHEM SOC, V129, P10336 TERADA M, 2007, J AM CHEM SOC, V129, P292 TSAI M, 2005, J AM CHEM SOC, V127, P14130 UNNI AK, 2005, J AM CHEM SOC, V127, P1336 URAGUCHI D, 2004, J AM CHEM SOC, V126, P11804 URAGUCHI D, 2004, J AM CHEM SOC, V126, P5356 VAYNER G, 2004, J AM CHEM SOC, V126, P199 WENZEL AG, 2002, J AM CHEM SOC, V124, P12964 WIECZOREK R, 2004, J AM CHEM SOC, V126, P12278 WIECZOREK R, 2004, J AM CHEM SOC, V126, P14198 WIECZOREK R, 2005, J AM CHEM SOC, V127, P14534 WIECZOREK R, 2005, J AM CHEM SOC, V127, P17216 WILLIAMS RM, 1992, CHEM REV, V92, P889 WU YD, 2001, J AM CHEM SOC, V123, P5777 XU YS, 2006, MOLECULES, V11, P666 YAGER KM, 1994, J AM CHEM SOC, V116, P9377 YAMANAKA M, 2007, J AM CHEM SOC, V129, P6756 YANG S, 2006, CHINESE J CHEM, V24, P1581 YU ZX, 2003, J AM CHEM SOC, V125, P13825 YU ZX, 2004, J AM CHEM SOC, V126, P9154 ZHANG GP, 2006, J FLUORINE CHEM, V127, P48 |